Chapter 1: I'm Not Flying
I'm sitting pretty and I don't know why
I found somebody, said he'd make me fly
Wrapped me up in ribbons then he left me to die
Wrapped me up in ribbons then he left me to die
- "Ribbons" by Ingrid Michaelson
Far too many maudlin thoughts paired with far too much alcohol leave Dan reacting slower to Serena’s advances than he should. He doesn’t push Serena away the first time she kisses him, (he’s sad enough to embrace his worst instincts and simply enjoy being wanted) but when she leverages herself onto his lap, he pulls back.
“Why?” she asks, tugging on his hair to angle his mouth towards hers.
He pushes her shoulders gently. “We can’t do this.”
“Yes we can.”
He pushes her away again, firmly enough this time that she slides off his lap, her heels clicking on the floor. “We shouldn’t. Blair —”
“Blair is with Chuck right now. You saw the pictures.” She slides a hand up his thigh to the waistband of his dress pants, hooking her fingers and tugging at his belt. Dan grabs her hand and drops it back down to her side. Blair is with Chuck right now. He’s going to be sick.
“Not that drunk.”
Whatever flattery he felt at Serena’s initial pursuit of him gives way to wariness. It’s not like Serena to be so dismissive of him. Or of Blair, for that matter.
“Serena, what’s going on here?”
She freezes for only a second and then shrugs, trailing a hand up his chest. “What do you mean?” It’s such a poor attempt at faking nonchalance. That more than anything tells him his instincts are right. They’ve all lied to one another enough over the years he recognizes it clearly.
“You’ve had plenty of chances to tell me you still want to be with me. Why now?” Serena avoids eye contact and reaches behind him for her phone propped up on the bar. She fiddles with it, turning it over and again in her hand, and then stuffs it in her bra.
“It seemed like a moment. That’s all.”
“Is this about your mom? Did she say something to upset you?”
Serena backs away from him, “Wow, Dan. I don’t have to listen —” she abruptly stops her sputtering, all pouty lips and hurt wounded eyes. He reaches for her hand to bring her back.
“Is this about Blair?” Serena flinches and something leaden and certain settles in his gut. Dan nods, exhaling a heavy sigh. “You’ve been weird about her all night. You were going to tell her, weren’t you?”
“I can explain.”
“You were going to tell her if we slept together?”
He heads for the door, hastily buttoning up his shirt as he puts distance between them, likely missing a few holes along the way. He doesn’t slow down even as he hears her follow.
“I wasn’t lying about loving you, Dan.”
He turns on his heel and Serena startles a little at his abrupt change of direction. “When did this become normal?” She looks confused, her brow furrowed. “All of us doing this shit to each other? How is this normal?” It’s not something she can answer, he knows that, but he still waits to see if she’ll say something. When she breaks eye contact, looking down at her shoes, he leaves the bar.
He gets into the first cab that pulls up and lets the driver go for a few blocks before he settles on a destination. Back to the loft, a bar, or heading straight to the airport and leaving for Rome immediately — all those options appeal but he settles on The Empire. There’s not a particularly good reason for it. If Serena and Gossip Girl are right the Chuck and Blair reunion tour has started. The last thing he wants is to witness it but he has to know.
Once he arrives at The Empire, Dan’s nerves fail him. He can’t bring himself to go into the building and he finds himself standing off to the side of the entrance taking deep breaths. He keeps telling himself anything will be better than the not knowing, but still he stays where he is.
A black sedan pulls up to the curb at the exact moment Chuck Bass storms out of the building and gets into it. If he wasn’t so depressed he’d be impressed at the synchronicity of it all. Blair must be close behind but the car pulls away from the curb without any indication Chuck was waiting for someone to join him.
Maybe Gossip Girl got it wrong. Maybe Blair only went to The Empire to end things with Chuck once and for all. The shard of hope barely forms before Blair is running out onto the street. She looks devastated, her eyes wide and watery, but she is still so painfully beautiful.
“Miss Waldorf, Mr. Bass just left,” the doorman informs her.
“Did he say where he was going?”
Dan would like nothing more than to slink away without talking to her, but she turns and spots him. He does everything he can to keep his expression blank, their eyes locked on one another. When Blair flicks her eyes to where Chuck’s car was, like she’s considering running after him, that’s all Dan needs.
He nods, doing his best to smile. His cheeks feel stretched thin — everything feels stretched taut and thin — wonders exactly how maniacal he must look.
“Okay,” he says, mostly to himself. Whatever he’s feeling must be akin to relief because a bit of the dread that’s been lodged in his gut all night releases. He doesn’t have to worry about Blair leaving him for Chuck anymore — it’s happened. And yes, it’s excruciating, but it happened. It’s over now. He can move on.
A long walk home suddenly sounds like the best idea he’s had all night — maybe enough walking will burn off all the alcohol and this feeling. He’s made it a block when he hears her run up behind him.
“Dan!” He tucks his chin to his chest and speeds up his steps. “Dan, stop! I can explain.”
Hearing the exact words Serena said to him is what gets him to stop. She runs in front of him, her chest heaving as she breathes.
“You missed the party,” he says. Now would be the time for her to offer that explanation, but as she struggles to find the words, he finds he doesn’t want them. What truth could they possibly illuminate?
“I know,” she says, shifting from heel to heel.
“You want to be with him?” Blair stops fidgeting and stands up straight, her eyes locked with his. She nods. “Well then good luck, I guess.”
He turns away again.
“I didn’t want this to happen. I —”
“What did you want to happen? How did you see this ending?” It’s another question she doesn’t have the answer to and Dan stops his frantic question asking to take another deep breath. He knows better than anyone what she’s been through these past two years. So many things she wanted and expected for her life got blown up or taken from her.
“Look,” he says, “I was wrong.” This admission clearly surprises her but she doesn’t say anything. “I thought I knew what Chuck meant to you, but I obviously don’t get it and it wasn’t fair for me to —” He runs a hand over his face, exhausted. He needs a vacation. Just say it. “This might make me the world’s biggest sucker for even suggesting it, but I leave for Rome in a week.” She knows all this — she’s the one who deployed her series of color-coded spreadsheets to meticulously plan their trip.
“I know,” she says.
“And you still have a ticket.” Blair’s eyes widen as she takes in his meaning, and then Dan feels embarrassment heat his face. Oh, god. He waves his hands, backing up, trying to erase the words from the air between them. “You know what, forget I said anything, just — go find Chuck.”
The day after she potentially loses three of the most important people in her life, Blair sits in her room paralyzed by the suddenness of the events. She keeps refreshing her email and checking Gossip Girl, but sooner or later she needs to leave her room. Running away to Paris with her mother is a tempting prospect.
Serena invites herself into the room as Blair is tracing her fingers over the details of her ticket to Italy. Last night she told Serena she wanted her gone for good and yet here she is. There’s something comforting about the fact that she and Serena are never really through with one another. The thought confuses her because the same idea when applied to Chuck often depresses her. Their eyes meet in the mirror as Serena sits on the edge of her bed. Usually it takes them a bit more time to come back together, though. Either Blair’s threats are taken less seriously than they used to be or Serena’s gotten more adept at navigating them.
“What are you doing?”
Against every self-preservation instinct she has Blair finds she wants to talk about this with her. “Dan won’t answer my emails.” She turns around, still holding the ticket. “What are you doing here?”
“I came to tell you something.”
“Oh. You have more to say about how I’m the worst person alive?”
“No, this is actually about how I am.” Serena tucks a strand of hair behind her ear and worries her lip as she stalls. “Last night I told Penelope to keep you away from the Shepherd’s divorce party for as long as possible. And then I got Dan drunk, which wasn’t hard since he was convinced you were going to breakup with him.”
“Why would he —?”
“Because I told him you would always be in love with Chuck.”
Blair looks away and back down to the ticket. “What —?”
“It’s the truth isn’t it?” Blair doesn’t respond. “I was going to film it.”
Serena’s being vague but her intentions are clear enough. It makes Blair feel nauseated how all of their love for one another has gotten twisted into this. She used to think it was just Chuck but really it’s all of them.
“You certainly have a thing for sex with my boyfriends at the Campbell Hotel.”
“Is Dan still your boyfriend?” Blair doesn’t say anything, just runs a finger along the edge of the ticket and shrugs. No, he’s not. Saying it out loud isn’t something she’s ready for.
“Honestly? To hurt you. But I also thought I could prove to Dan the two of us should be together.”
“S, that is so —”
“Look, neither one of us can claim the high ground after last night.” She gestures to the plane ticket. “What’s that?”
“My ticket to Italy. Dan still wants me to go with him.” Maybe it’s a cruel thing to admit. Serena is in love with Dan and wants to be with him. Last night Blair chose Chuck. And yet Dan still wants to be with her.
“But he knows you were with Chuck last night.” Blair nods. “Then why would he think —?”
“Because a week ago I told him I wanted nothing more than to spend the summer with him. And because he’s Dan Humphrey he believed me.” Stupid Dan Humphrey with his softly spoken ultimatums and the audacity to apologize to her for ever giving one in the first place. For letting her know it’s okay to be confused and telling her, in not so many words, that he’d wait for her to figure it out.
“Do you want to go to Italy?” Blair doesn’t even hesitate to nod. “So change your mind. Choose Dan. What’s the problem?”
“Gossip Girl puts Chuck in Monte Carlo. He is invariably doing something stupid, and ill-advised, and likely to blow up in his face. But I want to be there for him.” Serena sighs loudly and Blair has half a mind to take offense, but she gets it. When did they all become these predictable stereotypes? Serena reaches out to grab Blair’s hand. The contact makes her uncomfortable at first. “It’s the same problem I’ve always had, S: I want everything. Always at once, and never when I’m supposed to.”
They sit there for another minute, holding hands but not looking at one another. Eventually Serena takes the ticket out of Blair’s hand and sets it on the vanity. Blair looks up, startled by the action.
“You can’t go to Italy,” Serena says.
“Why not?” She can hear the tightness in her own voice. And oh, god, is she about to cry?
“Because you might want everything, B, but Dan doesn’t. He only wants you. It’s not fair.” Blair clenches her jaw, searching Serena’s words for ill-intent but there isn’t any. “Do you really want to be his Chuck?”
The question stings, but only because it might be one of the most honest things Serena’s ever said to her. She knows what it’s like to have someone reassure you of their affection only to change their mind in what feels like an instant — the very thing happened to her the night before. And, if she’s being honest, even if she went to Italy with Dan, she wouldn’t be able to promise him she’s done with Chuck.
She picks the ticket back up and sets it inside her vanity. Shuts the drawer tight. “You’re right,” Blair says. “I don’t belong in Italy.”
Dan observed it once himself: the force between her and Chuck is undeniable. They’re going to keep being drawn to one another and, if she goes to Italy, Dan will perpetually be caught in the middle. Unless she refuses to let him be.
After the events at The Empire Dan expects a sleepless night, but he falls asleep as soon as he lays down. He wakes up 12 hours later feeling a little like he’s sleeping off a hangover, which isn’t entirely inaccurate, he supposes. The past two years are a little fuzzy and maybe he’s been drunk if he thought falling in love with Blair Waldorf was a good idea. It’s as reasonable an explanation as any.
Once he has placed an excessively large and expensive Seamless order (if ordering close to $100.00 worth of Chinese food isn’t a sign he’s nursing a serious heartbreak, he’s not sure what is) and then eating past the point of uncomfortable, he starts packing. It’s initially packing for the summer in Rome but afterward Dan finds he’s restless. He can’t stop moving but he doesn’t want to leave the loft. So he keeps packing.
He boxes up books he never intends to read again, clothes he hasn’t worn in years, and decor he doesn’t remember purchasing, then calls Goodwill to schedule a pickup. He packs away everything in his room not considered an essential and then lies on the bed for a while, staring at the ceiling and occasionally speaking a word out loud to hear the way the sound bounces off the walls of the practically empty room. He’s not sure what compelled him. He’s planning to be back in Brooklyn for his senior year at NYU. All he knows is when he’s done with this summer workshop he can’t go back to being the person he is now. He can’t keep drifting from falling in love with one Upper-East-Side socialite to the next only to be crushed each time. The definition of insanity, and all that. Maybe if he leaves gaps on his shelves and in his closet the Dan who comes back from Rome will have the actual physical space required to figure his shit out. The Dan who comes back can fill the space with things the person he wants to be needs.
Hours later he’s eating reheated egg rolls and drinking a beer, surveying his work, when his dad walks into the loft pulling two large suitcases behind him. He leaves them by the couch and Dan watches as his dad pulls out a beer of his own and then stands next to him in the kitchen, accepting the lukewarm egg roll Dan offers.
After a few beats of silence Rufus gestures to the stacks of boxes with his beer bottle. “What’s all this?”
“Blair chose Chuck Bass,” Dan says. There’s more he could say, of course, but at its most basic level that’s what happened. He gestures to his dad’s suitcases. “What’s all this?”
“Lily chose Bart Bass.”
Dan huffs out a laugh, shaking his head at both of them. “Not a good day to be a Humphrey.”
His dad reheats the containers of food and convinces Dan to sit down on the couch. Dan doesn’t think talking will solve anything or make him feel better, but he’s missed his dad and his presence is welcome.
“I guess thought I was immune to all of this,” Dan says at the end of his rambling. “But it got me.”
“What got you?”
“The whole Upper-East-Side thing. The games, the compromises, and obfuscation. All of it. I mean, I actually convinced myself that sending in tips to Gossip Girl could be considered a noble act.”
“Well,” his dad says in a tone that manages to both comfort and condescend at the same time, “in my experience it’s the people who say ‘never’ that end up being the most vulnerable.”
Dan frowns. “What do you mean?”
“You know. The people who say ‘I’d never cheat’ commit adultery. The people who say money doesn’t mean anything to them are the ones who sell out, and those —”
“—those who say they don’t care about Blair Waldorf fall in love with her.”
Dan focuses on picking at the label of his beer bottle.
“You’ll be okay, son.” It’s such a simple thing, but his dad’s words kind of make him want to cry. Instead he takes another swig of his beer.
“And what about you?”
“I’ve gotten over Lily before,” he says, dismissing the question. His dad’s tone is too casual, though. Dan knows he must be heartbroken.
He seems to consider the question fully and then nods his head in acknowledgment of the point Dan makes. “Well, there’s a first time for everything.”
After Dan got over the shock of finding out he was dating his dad’s ex-girlfriend’s daughter, the writer in him thought there was something incredibly romantic and literary about following in his father’s footsteps. Now, though —
Now the thought is merely depressing. What’s more, Dan is starting to think his big what-if love story doesn’t star Serena. He knows how that story goes — all the good, and the bad, and the in between. There’s no mystery to how and why his relationship with Serena ended. His story with Blair felt like it was just getting started. And if Blair is his great what if, then he’s doomed. Because as long as there is Blair there will be Chuck. He can’t handle the idea of Chuck Bass still being a part of his life when he’s his dad’s age.
The remainder of Dan’s week is spent helping his dad move back fully into the loft and running errands before his trip. If he can just keep busy, he thinks, then he won’t have time to dwell on the fact he actually asked Blair to consider coming to Rome with him.
The rational part of him — the part that recognizes Chuck and Blair rely on one another in a way that escapes him, and the part that never could quite believe Blair Waldorf was his girlfriend — that part doesn’t believe for a second she’ll show up to the airport. He’s ashamed to admit there’s another piece of him, small as it may be, that has taken the shape of a hope balloon and refuses to deflate. Dan is fairly certain it’s the same part to blame for kissing Blair the first time, or writing about her the first time, or thinking that telling her he loved her was ever a good idea.
He holds onto that piece of hope long after he’s boarded the flight and sits in first class waiting, staring at the door, trying to will her to walk down the aisle and take the empty seat beside him.
She offers him a small mercy and texts him she won’t be coming.
4:18 PM - Blair to Dan
Thank you for the invitation but I won’t be able to join you this summer. I wish you the best.
It reads like a form rejection letter and Dan has no idea how to respond. So he doesn’t.
His writing that summer is less than spectacular. Honestly, it’s not what he expected or counted on. Isn’t this the type of experience that defines a writer? Don’t artists exist solely for the opportunity to channel their heartbreak into great works?
The other artists in his cohort are inspiring, simultaneously shaming and challenging him with their talent. He asks a small group for an honest critique of Inside. It was an unpolished piece of fiction published without his consent and now that reality has disproved the entire thesis of the book (turns out Charlie Trout wasn’t destined to end up alone) he can examine it as something separate from himself.
He checks Gossip Girl a time or two, mostly to discern exactly how his international escape is being sold. Dan finds, except for his departure from JFK, nothing has been sent in about his whereabouts or his life. Apparently the world at large has decided the UES is finished with Dan Humphrey and as such they are no longer interested in his exploits and comings and goings. It’s not the worst feeling.
And he knows what are essentially paparazzi photos aren’t an accurate reflection of reality but he can’t stop looking at photos of Blair and searching for signs she’s okay. Is she happy? Content? The only pictures posted are of Chuck and Blair with hard determined stares fixed on their faces as they shuffle in and out of town cars and walk down the streets of Manhattan. Sometimes Blair has a hand tucked into the crook of Chuck’s arm, sometimes not. Dan doesn’t find the answer to his questions in the photos so he’s decided to trust finally being with the person she wanted is enough to make her happy.
The writing workshop ends and with it his time in Rome. He takes a day trip to Tivoli and while walking along the wooded paths of the park he receives a travel alert on his phone regarding a change to his flight to New York. Walking along the paths in Villa Gregoriana Dan has a panic attack. He can’t catch his breath and he gets dizzy, steadying himself by a tree before he sinks to the ground.
The thought of seeing everyone — dealing with the condescending, or the pitying stares of those who, up to this last year, he considered his best-friends. The thought that he’s going to have to pretend he’s okay seeing Blair with Chuck when he’s not — oh god, he’s not okay — isn’t something he can handle. What’s more, going back to being the person he was when he left — the kind of person who gave his girlfriend ultimatums, got drunk and almost cheated with his ex, and lost sight of what matters to him — he’s suffocating and it can’t happen. He rests his elbows on his knees, cradling his head in his hands, telling himself to calm down, to take deep breaths. That he’s okay. Once he’s properly scared a family visiting from Poland and dismissed the concern of a couple of local residents, he stands up and brushes the dirt off. He’s not going back.
The first call he makes is to his dad and, to his credit, Rufus doesn’t seem surprised. Next he calls Nate. Despite the almost constant tumult of Nate’s family they’re the most well-connected group of people Dan knows and if anyone has a connection in Italy, it’s him. After he hangs up with Nate Dan stares at his phone. He asked Nate to tell Serena he’s not coming back (that connection is still too fraught to make on his own) but there’s one other person he’d like to talk to about it.
Dan spends all night with the other authors pretending to engage in the jovial environment as they drink wine, celebrating their final nights in Rome, but really he’s thinking of Blair. Should he call her? Send her an email? Does he owe her that? It’s as he’s contemplating these things that he gets an alert from Gossip Girl.
Spotted, it reads, resident power couple Blair Waldorf and Chuck Bass meeting with real estate mogul Joshua Barnes for cocktails. Daddy Bass won’t be pleased. Do I detect another coup d’ếtat?
Dan transfers to Florence University of the Arts and enrolls in their creative writing program. It will require him to be in Italy for at least two years as not all of his credits will transfer from NYU, but he doesn’t particularly care.
He unsubscribes from Gossip Girl the day he leaves Rome. He never calls Blair.
Blair doesn’t know how she managed to forget but being a powerhouse is exhausting. Those final weeks and months of her senior year are a bit of a blur but her proudest accomplishment is graduating from Columbia. While it comes without the pristine academic record she originally demanded of herself, in the end she did it. It doesn’t matter how she go to Columbia in the first place — she’s the one who put in the work.
It’s far too loud to hear anyone specifically calling her name as she crosses the stage of Radio City Music Hall to accept her diploma, but she’d like to think Serena, Nate (his graduation ceremony isn’t for another four days), and Chuck are cheering her on. She can’t bother to think of the people (her mom, dad, and...others who will remain unnamed) who didn’t make it a priority to be here.
She and Chuck become the power couple of her fantasies. He manages to eke a way back into Bass Industries, biding his time until he can do more, and she spends her days at Waldorf Designs. He doesn’t want to be Mr. Blair Waldorf but she has no real desire to be Mrs. Chuck Bass. She wonders if this life they’ve carved out for themselves is the best possible ending to their story — each one of them working to out-strive, out-achieve, and out-accomplish the other person. But always coming back to one another.
Her dreams have, admittedly, been widely inconsistent over the past years. One year she wanted nothing more than to be a princess and the next to be a titan of industry. There was always a consistent through line, though. Above all she wants to be in charge and have others revere her. Which is what makes it so embarrassing to admit to herself she doesn’t deserve the job at Waldorf Designs. Her mother simply hands her something she at one time clawed for and she’s not ready. But now the job, the company, and all the responsibility is hers and she’s determined to succeed.
Except nothing in her narrative is going the way it’s supposed to go. The story she was always told is if you work hard, harder than anyone else, you’ll be successful. Blair is doing that. She’s following those steps. She’s working harder than anyone she knows and still she isn’t okay. Neither is Waldorf Designs, and she doesn’t know what to do about that.
She distracts herself from the company’s financial woes by developing a fashion line she has to believe will change everything. As she throws herself into that the rest of the business becomes harder to manage. Payroll isn’t processed correctly one month and her shop assistants threaten to quit after not getting paid. She has to cancel a heavily advertised trunk show for one of Eleanor’s designer friends at the last minute. Blair didn’t get word out early enough so a line of furious debutantes leave her store in a steady stream all day.
She tries to talk to Chuck about it but he doesn’t listen. Well, he kind of does. Offering her, “you’ll be fine,” conciliatory statements and nothing more. Blair understands why Chuck’s attention is elsewhere. He’s pre-occupied by the havoc his father is wreaking on his life and the business. So most days when he asks her about work she smiles and says it’s going great, and then asks Dorota to bring her another glass of wine.
But then he finds her late one night, typing away at her computer even as she’s crying about some new disaster related to the fashion line.
Something must click for him because he actually asks her, “How bad is it?”
“It’s bad, Chuck.”
He runs a hand over her shoulder and places a kiss there. “I’ll fix it,” he says. It’s everything Blair thought she wanted — him offering to rescue her. Instead she feels like a failure.
The following week they’re getting dressed up for an event Blair doesn’t entirely know the original purpose of. What matters is she knows what she and Chuck will be using it for. Chuck drapes a strand of pearls around her neck — their eyes meeting in her vanity mirror as he does.
“You know what to do,” he says.
And she does. What she needs to do is cozy up to a potential investor of Waldorf Designs. Once faced with his predictable refusal, Blair is to casually let it slip that she’s aware he was caught in a compromising situation with the daughter of the chairman of the board of his real estate firm. And wouldn’t it be the absolute worst if that information made it back to the board?
She leaves the party with the promise of a $1.2 million investment with only a 10% stake in the business and a twisted, dark feeling in her gut. This isn’t what she thought it would be like. This isn’t the kind of woman she thought she’d be. While Chuck sleeps soundly beside her Blair slips out of bed and goes downstairs to make herself a cup of tea.
She sits on the chaise, and chooses not to examine the impulse as she reaches for her phone: Blair wants to talk to Dan.
She’s had his number in Italy for more than a year — (For the record, it’s not like she sought it out. She and Nate were at the same event and he left her to acquire another drink. She happened to see the WhatsApp message from Dan and then happened to take a picture of Dan’s number and saved it into her phone.) — but this is the first time she’s done more than hover over his name as she scrolled through her contacts.
Dan answers long after she resigned herself to his voicemail clicking on, his voice low and gravelly, and — “This is an incredibly rude way to answer the phone, Humphrey.”
“It’s incredibly rude to call someone at 4:30 in the morning.”
“I thought you tortured artist types didn’t go to bed until after 4:30.”
“What would make you think I’m tortured by anything?”
It’s not fair. She’s woken him up in the dead of night and she still can’t catch him off guard. She lets the silence stretch out when she hears Dan sigh.
“What’s going on Blair?”
What is going on? That is actually an excellent question. “I hear you’re finally graduating this year and wanted to wish you congratulations.”
“Have you written any good books lately?”
She takes a deep breath. “My company’s in trouble. My mom’s company. I — well, I’m in charge now — and we’re in trouble. Have been for a while, and I’m too ashamed to admit it to my mom, and I know if I tell her she’ll take it away.”
“What are you going to do?”
“Chuck has a —”
“And I’m done.”
“What?” She doesn’t know why she mentioned Chuck’s name except for Dan wanted to know how she was going to fix it. This is what they decided to do. Because she and Chuck are a team.
“You’re seriously considering taking advice from Chuck Bass on how to save your company?”
“This is his world, Dan. He knows what he’s talking about.”
“Yes.” Yes, she repeats to herself. This is something she is certain of.
“Have you picked up a Forbes magazine recently, Blair? Is anyone, besides Chuck himself, praising his business acumen?”
It’s such an unwelcome thought she won’t consider it. “You can’t argue with —”
“Do you think Bill Gates, Jeff Bezos, Elon Musk — you think these guys did the things Chuck and his father do? High stakes poker games in Monte Carlo, bribing board members, arson?”
As soon as Chuck told her of his plan to save Waldorf Designs, it felt right. No, Blair corrects. It felt familiar. The problem is (the problem always has been) that Dan doesn’t understand. He doesn’t get that this is how the Upper-East-Side works. There’s a different set of rules required. “Well what am I supposed to do?”
“I don’t know, Blair.” For the first time he sounds tired. “But I don’t have to know because I’m not the one running a company at the age of 23. Read a fucking book and figure it out.”
It’s one of the meanest things he’s ever said to her. His honesty just makes her miss him. “Are you ever coming back?”
“It was nice talking to you, Blair.” Before she can say anything else or even return the sentiment, he hangs up.
She goes to bed furious and wakes up even more irritated. She tried to explain to Dan all those months ago what happened and he never responded to her emails. Where does he get off acting like the injured party? Like her calling him is some great inconvenience. Clearly calling him was a mistake. A mistake she is never to repeat.
On the way to her hair appointment, Blair (for absolutely no particular reason) finds herself stopping at a newsstand and picks up the most recent issues of Forbes, Bloomberg Businessweek, and Fortune. As she’s washed, highlighted, plucked and styled, she pours through every word of each magazine. When she discovers not even the latest scandal at Bass Industries has any words of dedicated ink she turns her attention to an internet search.
The result? No one cares about Bass Industries. Maybe they did at one time, but no one is remotely interested. In fact the business world at large seems to just be waiting for the entire company to fall so they can hack up the pieces for themselves. Which makes the fact that it’s been the ever present third party in her relationship with Chuck sting even more. What have they been working so hard for?
That night Blair makes some calls — first to the investor to inform him her hard drive was unexpectedly corrupted, all evidence destroyed, and she won’t need his investment. He’s wary, untrusting, and she can’t blame him.
Then she calls Epperly.
The night after Blair calls, Dan dreams of her.
It’s something that happened with startling frequency the summer he left New York, but rarely since. The contents of the dream are hazy and nonsensical in the way dreams always are. At first he and Blair are sitting at a table in the café Vanessa worked at back in high school, but then Blair takes his hand and pulls him outside, and he knows, even though it still looks like Brooklyn, that they’re in Florence now. He tries to ask Blair a question, but she shushes him as they go down alleyways, turn corners, duck behind pillars. The further they walk the more New York morphs into Florence, the Florence he knows, until they’re sneaking into a late night bakery Dan loves and purchasing a bag of croissants.
“Blair.” She presses a finger to his lips.
“Hush, Humphrey,” she says, and places a piece of the croissant on his tongue.
He wakes up.
Dan knows the dream doesn’t mean anything. Well, fine. It means she’s in his head again (or she never really left and he’s just now admitting it). As he walks from his apartment to his creative writing intensive, he finds his gaze darting from person to person, anticipating seeing Blair on any of the streets that have become so familiar to him. It feels like that day on the plane — waiting and hoping she’ll surprise him and be there. When she doesn’t show by the end of the week, he’s almost ashamed. It’s like he’s relapsed. And maybe it’s wildly stupid and impulsive but she’s invaded his life in Florence now and he decides he can’t be there anymore.
FUA doesn’t really have a formal graduation ceremony, but he uses some of the royalties from his book to fly Jenny and Rufus out for the week anyway. He tells both of them about his new life plan: he’ll move back to Rome, teach English at a lower secondary school in the day, and spend time writing at night.
His family looks at one another, seemingly deciding who is going to react first. His dad clears his throat. “You’re never coming back, are you son?”
“I make sense here. I like it.”
“You didn’t answer my question.”
There’s an exhibit for some obscure artist at a local gallery Rufus decides he wants to go to (and that Dan’s already gone to thrice), so Dan shows his sister around the city he’s fallen in love with. She looks less harried and beat down by the UES, younger than he remembers her looking.
“What have you been writing?”
He reaches for a piece of bread from their shared plate. “Nothing good.”
“You’re always so hard on yourself.”
“Not this time, Jen.”
“The same thing happened to me.” He looks up at her, puzzled. “I know it’s not the same, but it was like all my creativity got sucked into a vortex. Took me a while to get it back.”
“But you got it back?”
She considers the question as she nibbles on a piece of cheese. “I think so. Maybe. I’m working on it.”
“So are you still writing Blair?” He gives her a look because the truth is he’s not writing much of anything these days. He’s also afraid once he starts it’ll be Blair’s story that comes out and he doesn’t think he’s ready for that. Even after all this time. “Well, are you?”
He shakes his head. “Believe it or not, I am doing my level best to not fixate all my time and attention on a relationship that ended two years ago.”
She shrugs. “It makes sense.”
His sister agreeing with him never leads to anywhere good. He narrows his eyes as he takes a sip of wine. “What makes sense?”
“Why you might still be hung up on her. The two of you didn’t get any closure.”
“Closure is a myth, I’m pretty sure.” As he says that the first person he thinks of is Serena. Things ended just as if not more terribly between the two of them as they did with Blair. Does Serena experience a wave of nausea that comes on unexpectedly when she thinks about how they left things? Or feel guilt she’s not quite sure how to atone for? Dan doesn’t want that for her. There were in love at one time and kind of family for a short stretch.
Jenny interrupts his thoughts by flicking water at him.
“Well then write about me,” she says. “I’m fascinating.”
He rolls his eyes at her, and then again when she orders a cappuccino from the waiter long after 12pm.
As far as book ideas go, however, it’s not the worst one he’s ever heard.
Epperly was predictably reluctant to help Blair, but after she debased herself and begged, and begged, and then Blair reminded her that, oh yeah, Epperly once colluded with Chuck Bass in the most unprofessional of ways, she conceded. Help comes in the form of Epperly setting up a meeting between Blair and a boutique owner on the Upper-West-Side.
The exterior of Pipe and Row is vaguely familiar in the way all small boutiques seem to be aesthetically the same. Blair can’t fathom why the owner of this boutique is the person Epperly thought she should meet with, but after being with Emily Rose for less than five minutes Blair understands.
“The problem is,” Emily says, “you have no clue who the Waldorf woman is.” Emily flips through pictures of the designs Blair brought. “Who is your creative director?”
Blair maintains eye contact. This is her company. She has nothing to be ashamed of. “We’re kind of doing creative direction by committee right now.”
“That doesn’t work. A single person needs to know who this woman is, where she’s going, what matters to her, what excites and challenges and motivates her. Then, when you know who that woman is, you build your collection around her.” Emily takes a sip of her coffee. “And, frankly, this is something 19-year-olds at Parsons learn their first semester.”
Blair wants to bite back, badly, The thing is, she knows all of this. It’s just with more and more to manage in the business she’s lost the guiding voice that even got her the job in the first place. Instead of defending herself she bites her tongue to keep the words in. She takes a sip of coffee and a deep a breath.
“I took an unconventional path. The question is what I do now.”
“What I just laid out is your large-scale problem, but your short-scale problem is you have no understanding of the financial demands of your company, do you?” Blair shakes her head. “The first thing you do is call your accountant, setup a daily meeting with him and you get to know the profit and losses better than he does.”
“Okay. I can do that.”
“And then you tell him you want to cut your store in half.”
It takes everything in Blair to remain seated. “Excuse me?”
“I have great respect for your mother and what she’s built, but this is too much space, and the real estate too valuable. You split the space, rent it out, and you have an extra $50,000 coming in per year. Easily. You take half and use it on your website redesign and online presence.”
“It would be humiliating.”
“If you want to go the way of Betsey Johnson, by all —”
“Look, Emily, I appreciate —”
“I killed two of my stores before I made this one work, Blair.” That confession stops Blair from continuing both her internal and external diatribe. Emily takes a breath, nodding at Blair. “You don’t have to listen to me, I don’t particularly care if you do, but I know what I’m talking about.”
At the end of their meeting Blair asks to schedule another one. She feels good, a little more in control, but still slightly sick.
First she went to Chuck and asked what she should do to fix the problem, and then she asked Dan, and now it’s Emily taking control and directing her. It’s not that she doesn’t appreciate the advice, but she wants to know what to do and how to fix these things. She wants her instincts to be the what guides her. She needs to know how to fix this on her own.
Later that night she’s having dinner with Nate. It’s something they do from time to time and when she takes their entire history into account, it objectively doesn’t make sense. He cheated on her. She cheated on him. And yet here they are at Café Boulud entirely comfortable with one another. They’re friends. The type of friends who help each other. And share their connections.
“What’s with the look?” Nate asks.
“You’re wearing your ‘I need something’ look. Why?”
She swishes her cocktail around and makes her face completely impassive. Unreadable. “Possibly because I need something.” She takes a sip of her drink.
“Do you happen to know anyone from NYU’s MBA program?”
He laughs, taking a sip of his own drink. “Between you and Dan.”
“What?” He simply shrugs. “Please explain yourself.”
She hopes she struck the proper balance between insistence and apathy because the truth is that Gossip Girl has long ceased reporting on the Humphreys. She knows he’s stayed close with Nate. And, a few months ago, Serena mentioned Dan sent her a letter she was still too scared to open. But Blair goes out of her way to not bring him up, so this mention of him is something she latches onto.
“Look, when he moved to Italy he asked for my help, too. Wanted to know if I knew anyone who could get him in at the school he transferred to.”
“Well,” Blair says imperiously, “as much as I hesitate to do anything Dan Humphrey would consider a good idea, I find myself needing the same favor.”
Nate rolls his eyes and Blair knows she didn’t fool him. The time for pretending Dan meant nothing to her is long past. “NYU, huh? You realize you could get into Columbia just as easily, right? I’m sure Chuck could —”
“Look,” she says, cutting him off. “I want to do this on my own terms. I just need a name to send my application to. That’s it.”
Because she got into NYU on her own when she was an undergrad, but Chuck fixed it for her so she could go to Columbia. That year at NYU still rankles her. The way she treated it like it was such a waste and how when she looks back the entire year feels more or less like a failure.
It won’t correct everything gone awry in her life, but this is an opportunity for a do-over and Blair wants it.
All it takes is being back in Rome for a few short hours for Dan to become convinced he made the right decision. Rome feels like home in a way Florence never did. Everything about the city inspires him to write: his apartment, the architecture, the people, the fact that he’s a college graduate and the future is rife with possibility.
He’s happy (or mostly), settled (or trying to be), and feels like he’s breathing easy for the first time in years. Maybe that’s why it just fits when he meets Karen.
His job at the school doesn’t start for another month so he spends his days writing and visiting all the parts he missed last time he was in Rome, when he vacillated between being deeply depressed and entranced by the country. It feels good to reclaim the city and be inspired by it instead.
It’s on one such day, exploring a little further out of the city, that he sets himself up at a café table. He overhears someone with an Italian accent almost as terrible as his ordering coffee and he can’t help but snort. The woman turns around and glares at him, well aware he was laughing at her. Of course that’s how they meet. He offers to buy her coffee as an apology.
Karen’s also from the US. She works for a study away department at a university and is visiting a number of foreign schools to assess their programs for her students. She’ll also be leaving Rome in two short weeks. Coffee turns into dinner, turns into Dan walking her back to her hotel and them making out before she goes up to her room.
Karen is in meetings with reps from the universities for several hours each day which gives Dan plenty of time to write. Once they’re both done for the day they explore the city, enjoy long dinners late into the night and then, when the making out no longer satisfies either of them, she stays the night at his apartment. She’s funny in a way he isn’t used to — his friends from high school and college are of the biting commentary bent — but Karen enjoys bits and absurd statements that make him roll his eyes and laugh out loud. They know few things about one another because one person will ask a question, the other will respond with a half-serious comment, and then they banter back and forth, forgetting the original question in favor of getting the other person to laugh.
They’re back at the café they met, Karen answering work emails while he plugs away at a chapter of what might, thank the lord, be the makings of an actual book, when he finds himself asking her a question.
“Have you ever been in love?”
She stops typing and tilts her head considering his question. “I don’t think so.”
“No. I mean, there was a time I thought my college boyfriend and I might get married, but looking back I don’t really think it was love.” She shrugs. “I will one day, though. I’m not worried about it. I’m still so young.”
He looks at her with wide eyes. She makes it sound so simple. “What? Not properly romantic enough for your writer sensibilities?”
“No, it’s not that,” he says. He stops talking to run a hand through his hair and huffs out a deep breath. Through it all she looks faintly amused by him. “How old are you?”
“25.” She’s a year older than him. I’m still so young, she said. It might be melodramatic but Dan hasn’t thought of himself as ‘so young’ in a very long time. Maybe it was falling in love with someone with occasional substance abuse issues, or having sex with a teacher, or dating a movie star, or being fooled into believing he was a teenage father — holy shit, maybe he needs some therapy. All of it. Everything from his high school experience has made him feel so very adult. “How old are you?”
“Well, I hope you’re able to learn from my wisdom,” she says, then goes back to typing her work email. And that’s that.
He kisses her goodbye two nights before she is set to leave Rome. It makes the most sense as Karen’s next day is full with one final round of meetings with universities, and then she’ll need to pack before flying out early the next morning. She slips him her number as they say goodbye. “In case you’re ever in Malibu.”
“Why would I ever go to Malibu?”
She looks at him like he might be insane. “Uh, because it’s paradise, Daniel.” She gives him a quick peck, waves as she steps onto the elevator, and he leaves. On his walk back to his apartment Dan marvels that this is by far the healthiest relationship he’s ever had. Maybe the secret to healthy relationships is keeping them short enough he can’t possibly ruin them.
It also gives him hope maybe he’ll find it again and when he does it won’t have to be quite as tumultuous. He doesn’t know if he could emotionally survive another five years of dating the way he did in high school and college.
Blair always thought if her relationship with Chuck came to a final and bitter end it would be because they did something so completely unforgivable or destructive the other person would have to walk away. So terrible that confessions of love, and the top of the Empire State Building, and paying off dowries would do nothing to salvage them. Something like she slept with his dad. Or, he got someone else pregnant. Basically every imagined end she’s thought of is twisted up in sex and power.
In the end it’s something significant but relatively mundane: Chuck misses her graduation from NYU.
Intellectually Blair knows missing a graduation isn’t the biggest of deals. Her mom and dad missed her undergraduate one, after all. It was a one-year MBA program, not a Pulitzer. Except Blair managed to get Waldorf Designs closer and closer to the black while maintaining a 3.8 GPA, and she’s proud of herself, and she wanted Chuck to be there. It’s the kind of thing a soul mate should want to be part of.
It was a relatively last minute decision. The night before her graduation Chuck explained everything. There’s an opportunity to merge Bass Industries with a smaller startup, Dorsey Tech. The CEO is a technological genius and if Chuck acquires his proprietary algorithms, it would move Bass Industries forward in a way other companies would be fighting to catch up with. It’d also secure his future at Bass Industries forever as there would be no way the board would ever let him be ousted. Blair suggested he postpone the meeting, just two days, but he kissed her, offered nothing more than a “I can’t,” and left for his flight.
Blair doesn’t understand how this always happens — how can the world operate in such a way that the moment Blair wants Chuck to be with her is always the precise moment he can’t be? They’ve both had those moments where they’re willing to give up everything for the other person, but they rarely occur at the same time.
So instead she celebrates with Serena and Nate (the two of them trying the relationship thing again), Emily and Emily’s wife, and her father who came into the city for the event. Her mother told her months prior she wouldn’t be able to attend and that means everything actually — that her mother had her assistant look up the date and circled it on the calendar. That she told Blair well in advance and has made plans to celebrate as soon as she’s back in the city. The small group goes out to dinner ordering more food than it is physically possible to eat, and then Serena, Nate, and Blair go out for drinks.
There’s a part of her, however remote it might be, that doesn’t want to forever lose her connection to Dan. So when the three of them are still out past three in the morning and Nate receives a text from Dan (Nate is, apparently, planning a trip to visit him in Rome — there’s a twinge of jealousy Blair feels at this revelation) Blair doesn’t hesitate to say, “tell him I said hello.” Nate and Serena both go eerily still for a second and then the bartender announces last call and Blair makes her way over to put in one last order of drinks.
When she stumbles back to the table with a beer for Nate and house cocktails for both herself and Serena, she sees Nate dart a glance first to Serena and then back to Blair.
“Dan says congratulations,” he says.
The tenuous thread that exists between them now — she sent a message to Dan, he sent one back — makes Blair’s heart beat a little faster, but she wills herself to maintain a blank expression. She sips at her drink. “He might be from Brooklyn but don’t look so surprised. We’re civilized people.”
She pours herself into bed that night, chugging water and taking ibuprofen before laying down. When she wakes up, Chuck is home. She’s not entirely sure how she knows — there’s something in the way the air in their apartment moves when he’s there versus when he’s not — it’s intangible but she’s almost never wrong.
She ties her robe around her waist as she comes down the stairs and Chuck is sitting at the table, impassively drinking coffee as he reads the paper.
“When did you get back?”
“A few hours ago.” His eyes drift to her normal seat at the table and she sees it — a red wrapped gift with a large gold bow. She knew the gift would be there. The only question is how lavish this apology will be.
She sits down, sets the gift aside, and serves herself some strawberries. Chuck does that thing where he watches her but is also pretending not to, his eyes drifting between whatever he’s reading and her. Once Dorota takes the rest of Blair’s breakfast order and shuts the dining room door, Chuck sets his paper aside with a long-suffering sigh.
“I’m sorry,” he says.
She nods. He’s always sorry. Being sorry has never been the problem.
“How’d the meeting go?”
“We got there and discovered Alan Dorsey’s flight from San Francisco got cancelled. He wasn’t able to make it.”
“Interesting,” she says, pouring herself a cup of coffee and taking a long, slow sip. “So you went for nothing, then.”
“I had to try, Blair.”
“Of course you did.” She knows Chuck loves her, but he also loves Bass Industries, and she’s starting to think between the two of them she’ll lose every time. The silence lasts long enough to get uncomfortable and it sends a little thrill up Blair’s spine as she eats her fruit and sips her coffee.
“Are you going to open your gift?”
The honest answer is she couldn’t care less, but she sets her cup of coffee aside and pulls the ribbon from the box. “Plane tickets,” she says. So the answer to her earlier question is fairly lavish. Despite Chuck’s cavalier attitude he seems to understand he really messed up this time.
“Three weeks, just the two of us. First Morrocco and then Spain. I already rented a house in —”
She sets the tickets aside. “It sounds wonderful but I have other obligations.”
He looks incredulous, and she wonders if he thinks she’s playing some sort of game. “Excuse me?”
“You have us leaving next week.”
“Dinner and drinks are nice, but this will be a real celebration.”
“I can’t leave, Chuck. I’m interviewing design interns next week.”
“You’re Blair Waldorf, if you want to go to Morocco then go to Morocco.”
“I don’t want to go to Morocco.”
“Well then what do you want? I’m trying to make this up to you.”
“It’s not that hard to understand, Chuck. I want you to stop having to make things up to me!” Dorota must have been listening at the door because she perfectly times bringing in Blair’s breakfast with the uncomfortable silence that stretches out between them.
When Blair finally looks at Chuck he stares back like he doesn’t recognize her.
“Why haven’t you ever asked for my help?”
“I ask for your —”
“You ask me to help you scheme, plan takedowns, crush our mutual enemies beneath our feet. But you’ve never once asked me for help with Bass Industries. Why is that?”
He smiles at her, sweetly, and she wants to throw her coffee cup at the wall. She and Chuck are the same in this way: if their expression is sweet, the emotion motivating it is likely twisted and dark.
“There’s not much overlap between the world of real estate and the world of fashion,” Chuck says.
“Business is business. I just spent a year of my life getting my MBA while running a company and —”
“Look, Waldorf Designs is an admirable and worthwhile venture. But Bass Industries is worth close to 1.8 billion —”
“And Prada is worth $5.5, Dior $4.9, Ralph Lauren over $4, surprising given their commitment to the whole Polo shirt thing, but you get my point.”
“How long do you think it will take to get Waldorf Designs anywhere close to that level? Our future lies with Bass Industries.”
She tilts her head, considering Chuck in his perfectly tailored suit at 9:00 AM. “When was it exactly, Chuck, that you cast me in the role of your vapid trophy wife?”
“I have never —”
“You indulge me.”
“No, I’m your partner. You’re not mine. I needed a partner with me last night.”
“I won’t see us become our parents, Chuck.” That stops him from saying anything else and he slides his chair closer to her, reaching for her hand.
She holds up the plane tickets. Exhibit A. “So tell me what happens when we go to Morocco and you get a call that Alan Dorsey is flying into New York? Will you drop everything and go? Maybe leave me by myself in our big rental house and promise to make it up to me. Again?” She looks around the room. “We live in the apartment that saw my parents’ marriage dissolve. We’re running the companies our parents built. I’ll tell you how this story ends. We’re both going to keep working 70-hours a week because our work actually means something to us but we will never truly sacrifice anything for one another. Ever. Then one of us will have an affair. Maybe both of us. I get pregnant and then, for the third time in my life, I have to wonder about the paternity of my child. If it’s yours we decide to stay together, make it work. But we’re not forgiving people, Chuck. We will never forgive each other. If we have a daughter, our relationship will be as fraught as mine is with my mother. And if we have a son, your relationship with him will be as bitter and exacting as yours is with your father —”
He slams his fist on the table, silverware and china clattering. It’s all so predictable. Blair doesn’t even flinch. “You don’t know that,” he says.
“So you see us being warm and fuzzy parents? The —” she searches her mind for the name of a good parent and can only come up with one, “Rufus Humphrey of the Upper-East-Side?”
“We could be.”
“Chuck, you couldn’t even make it to my graduation.” She wipes her mouth with her napkin, stands up, and pushes her chair in. Doesn’t kiss him on the forehead or squeeze his hand in reassurance. Just sets her plate aside and walks upstairs.
“You know,” he says. “Every time you and Serena stopped speaking and she would leave for parts unknown — every time she pulled one of her stunts you would swear you hated her. But you never stopped speaking about her. Or to her.”
She tenses her shoulders, certain where this conversation is leading. “So?”
“So what does it mean that that’s the first time you’ve even come close to mentioning Dan Humphrey’s name in the past four years?”
Blair is reminded of a time a few years prior when Serena said something similar to her about Dan — whenever you have feelings for someone that you can't deal with, you avoid them. At the time she insisted Serena was wrong. And now she’s just so tired of pretending.
“I don’t know,” she says. “You’re Chuck Bass. It can mean whatever you want it to mean.”
After a year at Central Saint Martin Jenny surprises the entire family when she transfers to a much smaller fashion design program on the west coast.
“London was basically New York with better accents,” she explained. “I need something different.”
Portland is by definition a big city but when Dan comes out for Jenny’s graduation he marvels at how vastly different it feels from New York. It’s so green and there’s so much space, and it makes New York’s coffee snob culture look laid back and chill. It’s the first time Dan’s been back in the states since he left and it takes some adjusting to not hear Italian everywhere he goes.
The run up to Jenny’s commencement is predictable: family dinners their parents try to remain civil throughout, helping pack up her apartment for her move back to New York, and meeting her awkward but affectionate visual design boyfriend. After the big event Dan stays for an additional week. It’s both a way to take a break from his school year ending and to spend time with his sister. They used to tell one another everything, and while he thinks it’s okay they no longer do he wants their relationship to be more than it is.
There’s also something he wants to show her.
They’re eating dinner at one of the city’s food cart pods, sharing a bit of everything from each cart, when he hands her an envelope containing the final draft of Is Aubrey Jessup Okay?
She frowns as she opens it. “What? Is this a contract Blair and Chuck want me to sign before I come back to New York or something?”
Maybe it’s a testament to how much he’s grown that Dan just laughs at the mention of the couple.
“No. It’s nothing like that.”
She pulls out the pages and looks from the title page to Dan and back again. “You wrote another book?” Jenny sounds stunned by this revelation and he gets it — the last time they talked about his writing he revealed how blocked he was.
He nods. “Believe it or not, I took your advice.” She squints, not seeming to remember. “It’s about you, Jen. Well, it’s kind of about you. It sort of started that way. And then Aubrey became her own person, but yeah.” She doesn’t seem to know what to say so he rushes to fill the silence. “Look, I told Alessandra I’ve been working on something but she hasn’t seen it yet. I want — you should read it first. And if you don’t want me to publish it, I won’t.”
“You wrote about me?” He nods and she just shakes her head. Dan waits for her to process and share with him whatever it is she’s thinking. “How long have you been working on this?”
“About a year. A little more than.”
“And you’d scrap the whole thing?”
“You’re my sister.” He knows there was a time that wouldn’t have mattered — he would have burned every relationship he had to the ground if it meant getting something published, but the self-righteous platitudes of his father must have finally sunk in because that’s not who he wants to be. He refuses to believe what Vanessa said all those years ago — he won’t sell his soul just to sell his art.
“So should I —” she holds the pages up.
“Yeah. I was thinking of driving out to the coast tomorrow. You know, try to distract myself from the fact you might hate it.”
“I’m not going to hate it.” After dinner Dan walks her back to her apartment and they hug before she goes inside. “Call me when you get back?”
Dan can see why so many novels about self-discovery and women having their post-divorce mid-life crises take place on beaches like the ones in Oregon. Something about the cliffs and the way it never gets quite warm enough to sunbathe makes everything feel so much larger. He gets fish and chips from a stand that is, inexplicably, on a boat and then spends most of the day walking as far as he can. When he gets tired, he sits and stares at the fading light on the water. His mind is wonderfully quiet for once.
It’s close to midnight when he finally gets back. He’s already texted Jenny to tell her he’ll call the next morning, but she’s waiting for him in the lobby of his hotel. She hands him back the pages.
Every thought he pushed aside comes roaring back. What if she hates it? What if she says no? What if he never gets inspired again? Is he doomed to have his only book be something he didn’t actually want published in the first place? He rubs a hand over his face and huffs out a heavy sigh. For some reason Blair comes to mind. She’s the cruelest and most honest critic he knows — what will she think of it?
“A girl wakes up three-hundred miles from home with no memory of who she is or how she got there? The metaphor is a little heavy handed,” Jenny says. “Don’t you think?”
“Jenny, look —”
“I loved it, Dan.”
She nods and then hugs him tight. “Thank you.”
He sends it to Alessandra the next morning. Less than an hour after he sends the email she calls him. “Daniel Humphrey I could wring your neck.”
“Why?” He pulls the phone away from his ear and looks at the caller ID. Maybe it’s not Alessandra? Why would she be mad about him sending her a book?
“Where did this come from?”
Oh. “I told you I’d been working on something.” He clears his throat. “So, it works?”
“Part coming of age novel, part mystery, part road trip comedy? It works. I’m not going to be able to convince my team to slot it into the publication schedule this cycle but how does next spring sound?”
She could have said six years from now and it would have sounded great to Dan. “Perfect.”
Dan realizes that, unfortunately, perfect is a bit of a stretch. Perfect would allow him to publish this book and keep the life he’s so carefully constructed intact. Maybe when you’ve published more than one best seller you can tell your editor how things are going to be, but he’s not there. Alessandra tells him they’re aiming for an April publication date and she desperately wants him in New York starting in March for promo. Well, she says ‘wants’ but he recognizes it’s not a request.
He talks to his school in Rome and amends his contract so he’ll teach for fall semester only, and then Dan will be done.
“You should move to Portland,” Jenny suggests one night over Skype. “I think you’d like it.”
“You want me to move to Portland just after you moved back to New York? Should I be offended?”
“Do you really want to come back?” Dan considers it seriously, does he?, and then shakes his head. “You’ll love it big brother. Be prepared to get really invested in micro brews.”
Once they hang up Dan can’t stop thinking about what Jenny asked him. Does he want to go back to New York? The city is actually quite small — not in terms of the number of people who live there but in terms of space. It’s surprising how often you run into someone you know in that mass of humanity. There’s a large part of him that isn’t concerned by that. He’s still friends with Nate. He’s not sure if he and Serena will ever be close again but they’re at least in a place where he wouldn’t feel weird seeing her. His story will always be connected to hers, and he’s more okay with that than he thought he’d be.
It’s the rest of it. (The people he does his best to avoid thinking about. The people he desperately hopes figured out what it takes to be happy. The people he knows he’ll have to stop himself from sending a copy of his book to.) He just needs more time.
Chapter 2: Getting Wise
You look so pretty in the dark of night
But I'm getting wise in the early light
I can see you falling like a homemade kite
I can see you falling like a homemade kite
- "Ribbons" by Ingrid Michaelson
Blair has never considered herself to be a lucky person. Opportunities don’t just come her way — she makes her own luck. But it is truly a turn of fortune that the final end of her relationship with Chuck times well with the end of Gossip Girl.
The 20-year-old son of a New York senator is caught with his pants down (with someone not his equally young wife) and the video is sent to everyone subscribed to Gossip Girl. It’s a commonplace event and not one Blair would even deem particularly noteworthy. Except the girl he was caught with was only 17 and the girl’s father is an attorney. A powerful one.
The FBI gets involved - distribution of child pornography not something anyone wants to mess around with — and then it’s over. The feds shutter the website, the person behind it gets three-years probation, a fine, and has to register as a sex offender for the rest of their lives. Everyone who has sent a tip into Gossip Girl in the past 10 years lives in fear of being subpoenaed, but the father seems content with having the website shut down.
A few copycats pop up in the absence of Gossip Girl but they never really gain traction. It seems everyone, even those people who found the updates titillating, grew tired of the spectacle. Or rather they grew tired of being made a spectacle.
Walking down the streets of New York, meeting up with friends, dating from time to time (normal people! who have never had sex with Serena!), all without the fear it will be posted online is hard to adjust to. Chuck moves out of the apartment and not a word is written about it anywhere — why would anyone deem a moving truck pulling up to an apartment building as noteworthy? That’s when Blair finally exhales. She’s even more thankful for Gossip Girl’s absence on the day she walks by a bookstore window to see a full poster display advertising the soon-to-be released book by Daniel Humphrey. She sees the sticker “Author of the NY Times Bestselling Inside” and her stomach flutters a little, remembering the words he once wrote about her. It’s been years since she read them, but they’re imprinted in her heart and mind.
She goes home and immediately pre-orders the book. A part of her — the narcissistic self-involved part of her she doesn’t think will ever die — wonders if she’s Aubrey Jessup.
Blair arrives home one day to find Dorota cleaning the living room while listening to an episode of Fresh Air over the sound system. She’s never known Dorota to listen to NPR and is about to tell her to turn it down when she hears who Terry Gross is interviewing.
“Aubrey shares a number of similarities to a character from your first book, Inside. You famously based your first novel on people you knew. Is Aubrey inspired by the same person as Claire Carlyle?”
Blair holds her breath, waiting for Dan’s answer, uncertain if she wants it to be ‘yes’ or ‘no.’ Dan doesn’t leave her guessing for long.
“No,” he says. “I was inspired by my sister, actually.”
“How’d that happen?”
“Well, she told me to write about her.” Terry Gross and Dan both share a laugh and Blair’s embarrassed she even entertained the possibility he’d still write about her. It’s been five years. “The way my sister and I grew up was a privilege. Really, it was. There’s also a lot about it that was hard. And my sister, she —.” Dan trails off and Blair can almost see him throwing his head back in the way he so often did as he tries to find the words. “I think it takes a lot of bravery to know what you want, pursue it relentlessly, and then keep going for it even after you get knocked down, one, two, three times.”
“By the end of the book Aubrey’s goals appear to have shifted. She doesn’t seem to be pursuing the same things she wanted in the beginning.”
“That’s one way to interpret it. I would argue sometimes our own motivations are a mystery to us. We think we’re pursuing something because it makes us happy when really it’s because it fulfills an unresolved need. And once we get what we actually want, what we actually need, the thing we initially pursued becomes irrelevant.”
“She’s not really a sympathetic character.”
“And neither is Holden Caulfield. Or, Dean Moriarty. Or, Becky Sharp. It doesn’t matter to me if the audience sympathizes with her. You can hate Aubrey for all I care but if I’ve done my job as an author by the end of the book, you understand why she made every choice she did.”
“Has your sister read the book?”
“She was the first person who did, actually.”
“And what does she think of it?”
By this time Blair has heard more than enough. In fact, the second she heard Dan’s voice it was probably too much. She clears her throat and Dorota reels around, dropping her dust rag with a guilty look on her face. “Your prolonged obsession with Dan Humphrey is starting to concern me, Dorota.”
Blair stomps off to her room and sits in front of her mirror. She wonders if that’s what Dan has decided happened between the two of them — was he the thing she pursued until she figured out what she really wanted? It’s what she knows most people think — Dan was a placeholder until she could be with Chuck again — but that Dan might think it doesn’t settle well with her.
Her copy of the book arrives in the mail at the end of the week and Blair stays up past 3am to finish it.
It’s like seeing her best-friend again after a long absence. She hears Dan’s voice in every word, but it’s different somehow. She remembers he didn’t get the chance to edit his first novel and this piece is much more refined. It’s also considerably more thoughtful. This is Dan Humphrey writing as an adult.
She reaches for her phone to text him but then remembers Nate mentioning Dan’s stateside again and all she has is his international number. On a whim, she texts his old number. Just to see if it works. She takes a deep breath:
3:21 AM - Blair to Dan
I read your book. Despite your tendency to split infinitives, it was well-written.
3:22 AM - +1(1)216116-11 to Blair
Error Invalid Number Please re-send using valid 10 digit number or valid short code.
Dan somehow convinces Alessandra to move the book launch party from New York to Portland. Being surrounded by cameras, press, and people dressed to the nines is a faint memory from a life that often doesn’t feel like it was ever his, but he’s startled by how well he falls back into it.
The party is less celebration and more of a long, pronounced, painful job interview where a lot of alcohol is served. The people from Simon and Schuster are waiting to see if he’s truly worth their time. The journalists and book reviewers are skeptical he has anything substantive to offer the literary world. And he hasn’t yet been in Portland long enough to have any friends. So it’s Dan being pulled around by Alessandra, introduced to another person he must meet. All he wants is to be back in his apartment in Rome — to go back to that hazy romantic time where no one expected anything of him.
As the night wears on, he finds the event isn’t as wearying as he feared. He meets a few people who already read the book and have a genuine response — mostly positive with some critique and that feels good. He’s much more comfortable debating ideas than he is mingling in an over-starched shirt.
At the end of the night he leaves the bookstore and decides to walk the two miles home back to his apartment. He passes by a 24-hour diner at the exact moment a group of high school kids dressed in formal wear rush in front of him, clearly ready for the milkshake and junk food portion of their prom night. The last person in the group to enter the diner is a girl in a bubblegum pink dress. Frankly, she looks ridiculous. Like she’s being swallowed by tulle, her head barely visible above the mass of fabric, but it makes Dan smile for the sole reason it reminds him of another girl.
He replays that day on the steps of the Met over and again on his walk home — the softness of her gaze as she looked at him, the feel of her hand in the crook of his elbow — and starts writing as soon as he steps through the door of his apartment.
The next day he meets Alessandra for lunch and she mistakes the red eyes for a hangover. She’s going over marketing strategy, his promo schedule, everything related to where and when he’ll be talking about Aubrey Jessup, but he’s having a hard time focusing on her words.
“What is with you this morning? You haven’t picked up any bad habits in Italy,” she touches the side of her nose, “have you?”
“Oh god, nothing like that. I started working on something new last night.”
“Already? Well, color me interested.”
He describes the general premise of the book to Alessandra but doesn’t go into much detail. He definitely doesn’t share who his inspiration is.
“When can I have a draft?”
“I just started it last night.” Alessandra is silent, merely raising an eyebrow, and it makes Dan laugh. “And that doesn’t matter to you at all, does it?” He takes a sip of his coffee to give himself a second to think. “Can I have some time to make sure this is something?”
If she’s disappointed by his answer she doesn’t look it. “Of course.”
It becomes rapidly evident to Dan this book is, in fact, something. He calls Alessandra the following week and tells her he can get the book to her by Thanksgiving. It gives him seven months, and maybe he’s being cocky but doesn’t even think he’ll need that much time. She keeps asking for his reassurance he’ll meet that deadline. “If I meet with the editor-in-chief and fight for you to be put into a fall slot, Dan, I need to know you can make it happen.”
“I can make it happen.”
At one point as he’s working on the first draft he decides to check out Gossip Girl to see if there are any pictures of the day that inspired the entire story. He’s surprised to see the whole website shuttered. Dan racks his brain for the last time he even tried to look at the website and can’t remember. He unsubscribed when he discovered he had no desire to be updated on the steady drumbeat of Waldorf/Bass drama. And that he was no longer considered a central figure to any of the happenings in New York.
When Nate visited him in Rome, he’d mentioned Blair and Chuck were done with one another. He knew Nate was gauging his response as he shared this information, but Dan only chuckled and responded with a “yeah, sure they are.” Nate insisted, though. He was tempted then to look Blair up but he never did.
He texts Nate, curious as to why no one mentioned Gossip Girl was no more. Nate’s response makes entirely too much sense.
5:47 PM - Nate to Dan
No one wanted to jinx it, man.
And it’s a relief - absolutely - he’s glad these people he loves and cares about and still considers friends (plus Chuck) aren’t being dogged anymore, but there’s a part of him that’s a little sad. There are plenty of souvenirs from his time with Serena but none from that fever dream that was his relationship with Blair. Sometimes he thinks he imagined the whole thing and now all evidence it existed — there was actually a time of Dan and Blair — is gone.
If he wasn’t motivated to finish the book before —
The entire shape of Blair’s life is different. In fact, it’s so distinct from anything she’s ever experienced sometimes she has to remind herself it is her life. She and Chuck have been well-and-broken up for a year and she can count the number of times they’ve run into each other with one hand.
She also has friends, well, a friend who is a bona fide grownup. Nate and Serena don’t really know Emily, and Blair has to admit it’s nice to have a friend who gets along with the people in her life but is separate from it at the same time. A friend who doesn’t know every detail of the more salacious parts of her high school and college days.
It also means Emily hasn’t learned to ignore the worst parts of Blair’s personality. She doesn’t let Blair get away with anything because Emily doesn’t know she should fear Blair’s wrath. Emily’s never been the victim of a Blair Waldorf scheme. During one of their monthly meetings Blair goes on a tirade about the creative direction of Waldorf Designs. About the way her mother will never let her have complete autonomy. It doesn’t seem to occur to Emily Rose to just give a sympathetic ear. Instead Blair gets —
“Why are you still working for your mother, Blair?”
“I’m the CEO of Waldorf Designs.”
“It’s a great opportunity.”
“It’s only a great opportunity if it’s what you want to be doing.”
“Well, what else would I do?”
Emily laughs. “You’re 25, not 80. You don’t have to have your career decided tomorrow.”
“You don’t know me at all, do you?”
That night Blair attends a party at the marketing firm Serena has started working for and finds herself alone at the bar, nursing a drink. It’s almost a relief to be in a room where she doesn’t know anyone. She can sit at the bar, be ignored, and think things through. Blair knows Serena invited her in the hopes she’d possibly find a guy she was interested in hooking up with, but Blair’s not there. The meeting with Emily consumes her thoughts.
She should want to run her mother’s company — it’s the kind of opportunity she dreamed of as a kid. If she’s honest with herself, though, it’s far from a dream job. It’s not even the best job she’s ever had. The best job she’s ever had was one she got before she could fully handle it. She drinks her gin and tonic and thinks about those late nights at W — what she’d do differently given the chance, what she loved most about the job.
She pulls out her phone and scrolls to Dan’s name.
10:08 PM - Blair to Dan
Emily thinks I need to leave Waldorf Designs. But I’m not sure if I’m ready.
She takes a deep breath and keeps typing.
10:09 PM - Blair to Dan
Between saying goodbye to Chuck, really saying goodbye, and then saying goodbye to Waldorf Designs. It’s like piece-by-piece the life I thought I was going to have, the life I’ve wanted since I was 17, is being pulled apart.
10:09 PM - Blair to Dan
Would it be crazy to walk away?
10:10 PM - +1(1)216116-11 to Blair
Error Invalid Number Please re-send using valid 10 digit number or valid short code.
“I could give you his number if you wanted,” Serena says. Blair’s hand shakes a little from the startle as she returns her phone to her clutch.
“Not necessary.” She turns on her bar stool to face Serena. “Also, it’s incredibly rude to sneak up on people. And to read their text messages.”
“You miss him.”
“You’re texting his old phone number.”
Blair shrugs and takes another sip of her drink. “You know how some people talk to themselves to figure out what they want? This is my version of that. Don’t read anything into it.” She’s using every tactic in her arsenal to convince Serena this all means nothing.
“Did you read his book?”
“I skimmed it.”
So, apparently Serena remains unconvinced. Blair primly folds her hands in her lap. “Okay, hypothetically, if I still occasionally, on the rarest of circumstances, thought of Dan Humphrey, why do you think that would be? For years we were barely friends and I haven’t really talked to him since he left, but...hypothetically.”
“Well, hypothetically, because towards the end he was your best-friend and you ended up treating him like he didn’t matter.” Serena runs a hand down Blair’s back in comfort and sits next to her. Blair takes a sip of her drink, always uncertain how to respond when Serena shows rare insight into her life.
“Maybe,” Blair answers.
“And then there’s the other thing,” Serena says.
“What other thing?”
“That he might have been your big love story.”
Serena’s words both cause her heart to race and make her feel like she might throw up. “That’s ridiculous, S. No one meets their big love story at 16.”
“I don’t know,” she says, and Blair knows Serena’s eyes are tracking Nate as he walks across the room to join them. “Some people do.”
Blair finds herself at Emily’s shop the next day. She doesn’t even let Emily say hello before Blair shares the conclusion she came to the night before. “I want to quit Waldorf Designs.”
Emily beams. “I knew —”
“And I’m going to recommend you for the job.”
It’s less than two weeks later that her mother and Cyrus are back in town. On a rare night where it’s just the two of them sharing dinner, Blair shares her plan. At first her mother thinks it’s a negotiating tactic — Blair angling for more control at Waldorf Designs. When Blair insists she’s being honest, that she’s stepping down, the reaction changes to incredulous.
“You really want to start over?” her mom asks.
The idea is novel enough to make Blair grin. “Absolutely.”
She commits to staying at Waldorf Designs through the end of July, and then intends to take the next month off before starting work- where, she has no clue - in the fall.
She’s 25 and for the first time since high school Blair has a plan completely of her own making. And no idea where it’s going to lead.
Dan fights with Alessandra and has to advocate for his new book in a way he didn’t need to with Aubrey Jessup. It always comes down to a central issue — Alessandra insists the protagonist needs to fall in love by the end of the book. And as many times as Dan explains Matilda does fall in love, Alessandra simply rolls her eyes because he knows that’s not what she means.
The book starts with a wedding between a common American woman and the prince of a small country. The two meet in graduate school in America. A year into the marriage tragedy comes when the crown prince dies. Upon his death it is expected by all that Matilda will leave the kingdom and return to America. It’s no secret her Royal Highness did not approve of her son marrying a commoner, and with her husband’s passing, Matilda has no true claim to the throne. Besides, they’re not even ruling royalty. There’s no reason for her to stay.
But then Matilda’s best-friend, Philip, convinces her to. She loves the country and the people of the country love her. So Matilda commits to ruling without a crown. It’s the love story between a woman and the country that welcomed her, but more that Dan believes it’s about grieving and moving on from the kind of love you always wanted. It’s about how we get to decide the end of our fairytale.
Alessandra wants Matilda and Philip to be the happily ever after — towards the end of her rounds of critique Alessandra gets desperate enough to suggest Dan just throw it into the epilogue. But Dan refuses.
He’s writing the fairytale he wishes he would have been brave enough to help Blair discover. What she needed most, always, was a friend who didn’t expect anything of her. Caught up in all of his own still-adolescent worries and his love for her, he hadn’t been able to provide that.
They agree on an ending ambiguous enough to satisfy them both. On the eve of the anniversary of the prince’s death, Philip flies out to meet Matilda. Before she steps out of the car to place flowers on the grave, she tells Philip she loves him. If people want to see it as romance, so be it, but Dan chooses to see it differently. Also, he’s the author, so fuck what everyone else thinks.
Jenny reads it and for every word of praise, she offers at least two mocking him.
Nate responds similarly. “Dan Humphrey, are you pining?”
Dan doesn’t know how to get people to understand this book is his do over. Philip isn’t him — Philip is the friend he wishes he could have been. When Jenny asks him, even more directly, if Matilda is Blair — he doesn’t know how to answer. He settles for vaguely pronouncing “it’s complicated” and then changes the subject to the new guy Jenny’s seeing.
Someone at Simon and Schuster leaks a page from the book and Dan panics that his writing is horribly transparent but, much to his consternation and amusement, most people assume it’s inspired by Kate Middleton and Prince William.
It’s enough to drum up interest, though, and Alessandra convinces him a book tour needs to happen — and this time it needs to start in New York.
Blair spends her month after quitting Waldorf Designs in France. She spent some of that time with her father, but the majority of it was on her own, travelling at her own pace and seeing the sites and museums she loves most. She’s never been very good at being alone - it’s something she’s actively worked on these past years.
She has a job lined up as Associate Beauty Editor at Vogue and she’s almost apoplectic with excitement when she tells her mom about it.
“Isn’t that a step down?” her mother asks.
Blair’s smile is bright and sincere. “Yes. It is.”
She’s back in New York for less than a day when Serena calls her and insists they meet for lunch at Gramercy Tavern. Serena wants to hear about the new job, and about France, and also she and Nate called things off again (in a completely normal and amicable manner this time) so she needs to talk through that. So, of course, Blair says yes.
There’s nothing strange or amiss about their interaction except Blair can’t help but feel Serena is withholding something from her. With the two of them and their complicated history that could truly be anything. She doesn’t particularly like the feeling. Serena confirms Blair’s suspicions when, rather than take a car back to their respective houses, she insists they take a nice long walk.
It seems harmless enough, as does the arm Serena loops through Blair’s, so she plays along as they stop at a bakery for coffee and pastries. It’s a delicate balancing act, eating macarons while drinking coffee, but it’s one she’s perfected over the past decade of her life.
Serena is clearly leading them somewhere but pretending not to. At a certain point they lapse into silence and Blair finds herself waiting for the big reveal — for whatever it is Serena has planned. Their final destination appears to be Blair’s favorite bookstore, and that’s enough to confuse her even more.
“What are we doing here?” Blair asks. Her birthday is still months away and as far as she knows neither one of them has done anything vicious enough to require amends in the form of gifts.
“I want to show you something.”
Blair sighs and makes for the front door, but Serena stops her by grabbing her hand and pulls her back.
Now she’s annoyed. “What?”
“Look Blair, what?”
“No. Blair, look!” Serena points to the window and it all becomes clear. She’s not sure how she’s supposed to respond but Blair is fully aware Serena is staring, waiting to see how she’ll react. “Blair?” she says, tentative and quiet.
“Dan Humphrey, you Brooklyn born bastard!” Blair yells, and then storms off. She has another book to order.
Once back in New York Dan’s first stop is Brooklyn. He is long overdue for a visit with his dad and then he’s off to his favorite bookstore. The event is a small reading and Q&A. Alessandra refuses to refer to it as the book launch as it is too nondescript for her taste.
If he had to do this, though — promote this story in this place he wants to start somewhere he’s comfortable. A place that reminds him of that first impulse to write.
There’s the expected questions about the inspiration behind the piece, one or two about the relationship between Philip and Matilda, and then the moderator asks a question he should have expected.
“You’ve published three novels and the central character in each has been a woman — is that an intentional choice?”
Dan had written Inside to be Dylan’s story, but the moderator isn’t the first to see the story as actually belonging to Claire. He thinks about the question for a second, his brow furrowed, and shakes his head. “No, I don’t think so. But the women in my life are some of the best people I’ve ever known. They’re brave in a way few men I know ever are. Or are ever required to be.” He pauses to point to his dad in the front row. “No offense, dad.” The joke gets the appropriate laughs in response and Dan lets himself think this whole book tour could actually be enjoyable.
The greatest relief is that the people who have read the new book seem to understand what it is he’s trying to do. What’s more, they seem to like it. He shares this musing with Jenny who rolls her eyes.
“Yeah, because people often come to a book reading for an author they don’t particularly enjoy hearing from.”
The NY Times book review comes out the next day, and while it’s mostly favorable, it mentions he’s hard to pin down as an author. Each of his books, they say, have been so widely different from one another. It’ll be hard for him to develop a following if he can’t be connected with a specific genre. Dan finds he doesn’t mind being hard to peg.
What Alessandra refers to as the official book launch is scheduled for the largest reading room of a bookstore in downtown Manhattan. It’s a ticketed event and while it’s not sold out, she’s shown him the numbers and the room is going to be full.
Nate and Serena both texted about attending, but maybe Dan has PTSD from the last time they attended one of his book events because he convinces them to just take him out to lunch the next day.
“Think of it as a private chat with the author,” he texted them. “In a silent auction that prize would go for at least 20 bucks.”
Even without them, more than 200 people have bought tickets to hear him read from his book and share his thoughts on art, writing, and his process.
He gets to the store a couple hours before the event is due to start but finds himself frozen outside. Something about seeing the cover of his book blown up to window size is surreal and makes it feel like it’s no longer the thing he created. The cover depicts a woman standing on a large stone staircase. The photo is of her back so her face is hidden from the reader. A diaphanous pink gown swirls around her feet and cascades down the staircase. A glimpse of a tiara is visible and Dan likes that from the tilt of her head you can’t really be sure of where she’s looking. What she’s focused on is a mystery to everyone. Almost Queen is the title he and Alessandra settled on and he likes the melancholy pair the image and the title make.
When he goes inside he’s surprised to find a line already forming. It might be a ticketed event but seating is still first come first serve.
Alessandra keeps trying to get him to leave the book display for the signing afterwards alone, and the manager of the bookstore echoes her wishes. He needs to do something to keep himself occupied. He’s explaining this to Alessandra, again, when he hears a set of determined footsteps behind him.
“You came back.”
Dan turns around and while a remote part of his brain tells him to play this moment cool, he can’t help but grin when he sees her.
Blair, always fated to be his exact counterpoint it seems, is scowling. She holds up the book, her expression clearly asking ‘what the hell?’
“I could sue, you know.”
And there’s something so wonderfully absurd that these are the first words they’ve spoken to each other in years he can’t help but laugh.
She does an admirable job of maintaining her ire for another stretch of seconds, but then she bites her lip to hold in her grin.
“I guess it’s a good thing I didn’t go with my original title, then.”
“Would you believe Matilda was originally Beatrice, and the book was Queen Bea?”
“I was never one for subtlety.” She looks down at her shoes, still smiling, and Dan takes the opportunity to really look at her for the first time in years. “You look good, Blair.”
“And you look shaggy, Humphrey. I guess some things don’t change.”
He’ll never understand why she can see these things to him and he finds himself charmed. She’s absolutely right - some things don’t ever change. He runs a hand through his hair.
“I’ve been telling him he should cut it for weeks now.”
Blair’s eyes go wide as she looks to Alessandra. It’s then the both of them, Dan and Blair, seem to remember they are in a public place being observed by those around them. He has to remind himself to breathe - that none of this will be posted to Gossip Girl.
“The event doesn’t start for another two hours,” Alessandra says. “But there are still tickets available.”
“Oh,” Blair says, looking away. “Of course. I — of course.” She looks lost for a second, like this isn’t going the way she planned. Dan is about to intervene, tell Alessandra to back off, but then Blair stops looking so lost and is back to being Blair. “So when should I come back?”
“No!” Dan says. It’s too loud and forceful, and Blair makes a face of surprise. “The event might not start for two hours but I could use a cup of coffee now.”
Blair tries, and fails, to hold in another smile. “I might know a place.”
“Dan, you should get ready for the reading,” Alessandra says.
“You’ve been trying to get me to leave for the past 30 minutes.”
“If you’re late,” she doesn’t finish the threat.
“I won’t be.”
And he’s not. But it’s a close thing.
He’s actually surprised when Blair stops their conversation to offer to walk him back to the bookstore. She also suggests she attend the reading but Dan dismisses the offer before she finishes speaking.
“I’d be too nervous, I think.” He hopes that doesn’t come out too harsh. “Is that okay?”
“No, I get it.”
Dan stands up, pushes in his chair, and leans across the table to kiss her on the cheek. “I’ll see you tonight, though.”
Once he presses his lips to her cheek, they both freeze, and then he kind of awkwardly chuckles. He’s not sure if he’s more embarrassed by the kiss or by acting out some domestic fantasy where the two of them have a standing dinner date.
“I’m sorry. Old habit, I don’t know where —”
“I could do dinner,” Blair says, stopping him before he can apologize even more.
He sighs in relief and smiles. “Good.”
When Blair imagined seeing Dan again — something she knew was inevitable though she never knew how or when it would happen — she thought their time together would include hours of rehashing the rise and ignominious fall of their relationship.
Except they’ve been together for four hours now, the conversation hasn’t stalled for even a second, and the past hasn’t been a part of it. But, she keeps wondering if she should bring it up, so maybe the past has been a part of it this whole time, which means —
“Whoa, where’d you go?”
“I’m right here,” she says.
“Uh huh.” Dan takes another bite of the chocolate souffle shared between them. She takes a sip of coffee, looks at the little smirk on his face which means he thinks he’s right, and god she just missed him.
“You’re quieter than you used to be,” she says.
“This thing happens when you get older, I think, which is you realize you talked a lot as an 18-year-old and half of what you said was utter bullshit.”
“Speak for yourself, Humphrey. I’ve always been brilliant.”
The restaurant is giving them that look which means they’ve been there for too long so they relocate to a coffee shop. He tells her about the book tour. She tells him about her job.
It’s 1am on a Saturday morning, and she should really be getting home. Plus she knows Dan’s had a really long day. As they’re considering whether they should leave or order something else, Dan mentions he’s in town for another few days. All Blair feels is relief. (And maybe the slight presence of anticipation and longing and the urge to kiss Dan Humphrey is mixed in there as well.) He’s staying with his dad but it feels natural for Blair to suggest he stay with her instead. It doesn’t make any sense. His stuff is already at his dad’s. Dan doesn’t have a change of clothes with him, but still she cajoles —
“Think about it, Humphrey. If you’re meeting Nate and Serena downtown tomorrow it makes the most sense.”
He smiles and nods like he knows what she’s really saying and accepts. “It does.”
She sets him up in the guest room — the room that used to be Serena’s — and they find themselves brushing their teeth at the same time in the shared bathroom. Once they’re both done, Dan just kind of smiles at her, looking nervous and uncertain. She bets he’s going to do that thing where he starts talking simply to fill the silence, without any clue as to what he actually wants to say.
Before he can start, she grabs him by the front of his t-shirt and pulls him into her room.
So much is familiar but in the best possible way: how Dan’s hands feel so big spread across the small of her back, the comforting weight of him as he presses her into the mattress, how he makes her feel safe and desired at the same time. There are other things she forgot, though. Like how Dan really has a thing for her lower lip. And how she can’t bring herself to stop touching him.
It’s bordering on a reasonable hour in the morning, neither one having slept yet, when Blair snuggles closer to Dan, their naked bodies sticking together in a way that isn’t nearly as unpleasant as it probably should be. “Why’d you write it?”
“I don’t really know,” he says, pulling her even closer to him. She feels herself start to drift off as she waits for his answer, Dan’s fingers trailing up and down her spine. “There are a few moments from my life that are so clear. No matter how old I get or what happens to me, I don’t think they’ll ever fade. They’re just so vivid. That day with you was one of them.” He kisses her temple. “I think I wanted to write it down to make sure it always would be.”
They spend the next stretch staring at one another, kisses shared from time to time, when eventually he asks her about the fall of Gossip Girl.
After she explains he goes silent but he pulls her closer so she knows he’s awake.
“Who was it?” he eventually asks.
“Former teacher at Constance.”
“We really got to start paying teachers more.” She laughs and kisses his chest. “So that’s all it would have taken?” It’s said quietly enough Blair’s not certain he intended her to hear it.
She looks up at him, resting her chin on his chest. “What?”
“To shut it down. Just a parent willing to do something.”
Blair hasn’t wasted much time on the ‘what ifs’ of Gossip Girl not being a presence in her life. The platform was not kind to her, but she used it when it served. There’s something unbelievably sad about what Dan has said, though. Everything could have been so much simpler.
But then she thinks about the life she’s built: the job that’s all hers, the friends that are all hers, and Dan beside her. How everything that led her to this point was anything but simple. If it meant giving any of those things up, Blair’s not sure she would do anything different.
Dan knew a long distance relationship with Blair would be hard. And, as much as he loves to be right, in this case it really sucks. At the same time it's not nearly as difficult as those years he went without admitting to himself how much he missed her.
They talk on the phone, and video chat, and text constantly. They also try their hand at phone sex but Dan will occasionally use a word that takes Blair out of the moment. She’ll stop trying to get him off long enough to lecture him on why it was an unacceptable choice and then resume like nothing happened.
He kind of zigzags the country on his book tour. When he has 3-days or more off in a row, he flies to New York to visit Blair rather than go home to Portland (the high school kid Dan pays to water his plants is thankful for the contributions to his ‘I need a new skateboard’ fund).
She surprises him in Chicago for his birthday and they’re both alarmed to find neither one of them has ever been there. They let themselves be tourists in a way they’re too embarrassed to be anywhere else.
The book tour takes him through spring and after it’s over he’s not sure what to do next. He writes a few short stories, because he likes the challenge of creating a fully realized world in the span of 20 pages, but he puts them all away in a drawer. He’s 27-years old, has published three novels, and he kinda wants to relax.
He takes a playwriting class just to try something new, and even a comedy improv class to help him build the skill of flexibility (Blair is adamant she will never attend an improv performance — ever). He teaches a writing class at the community college as an adjunct professor and wills himself to not be intimidated by the fact most of the class is older than he is.
When Dan tells Alessandra he’s going to take a break she drops him as a client. There’s some irritation but no malice in her response and she tells him to call her when he’s ready to publish something else.
After weeks and months of cajoling, Blair finally visits him in Portland. The entire week they’re together there’s an almost permanent crease in her brow. Dan finds himself smoothing it away with his thumb. Sometimes she smiles when he does it and her face relaxes. Sometimes she smacks his hand away. Eventually she reveals the source of her consternation.
They pass by a brewery operated in part on kinetic energy from bicycles stationed outside of the restaurant. “This city is like if Brooklyn just doubled in size.” And maybe that’s why he loves it.
He also loves her. All of that old feeling, and a whole host of new ones, woke up inside him the second his lips touched her cheek in that coffee shop the day of his book launch. But he waits to tell her. It’s not a power play, or because he’s angling for anything, but because he’s doing his best to hold her close but not too tight.
She has to know, though.
There are things in their relationship they never got to have before. Dan is greedy to experience all of them. Like working through what happens when someone double-books themselves and forgets they were going to talk on the phone, but nothing bad happened—it was just an honest mistake. And the negotiations for a holiday season. And discussions of anniversaries. It’s all so boring, but Dan wants it all.
On one of his visits back to New York Blair makes dinner reservations at a restaurant she’s meant to go to for months. She’s readjusting the knot of his tie while he does his best to distract her enough to get her to stop. To cancel all their plans. To spend it under her very expensive duvet.
“We could order takeout,” he offers, kissing her at the end of the suggestion.
“We could,” she says, and smooths down his tie. “But we’re not going to.”
“But we could.”
“If you wanted to do something other than go to this restaurant I have been talking about for weeks, maybe you should have mentioned it more than 30 minutes before our reservation time.”
Before he knows it this thing he brought up simply to goad her, to see her eyes spark, and allow him the opportunity to run his hands over the expensive fabric of her dress, becomes a real fight. They’re in one another’s space, with Blair’s hands curled up into little fists, her eyes narrowed, and he can’t help it. Even angry he doesn’t know if there’s anyone more beautiful than Blair. She’s in the middle of yelling at him when he reaches for her, kissing her even as she talks, stifling her words against his lips. He’s not expecting her to push him away — hard.
“Why did you do that?” she demands. And if he thought she was mad before, it’s nothing compared to what she looks like now.
“You looked cute.”
“Okay maybe not cute, exactly...”
She shakes her head and marches past him. He reaches for her wrist but she wrenches it out of his grasp. “Don’t touch me right now, Dan.”
“Where are you going?”
“To cutely remove myself from your presence.”
He follows her down the stairs but keeps his distance. Okay. The ‘cute’ thing was condescending. He can see that. But usually when he’s pretentious or condescending Blair simply out-condescends him. This is — well, he’s never seen Blair react like this.
She ignores him, steps into the elevator, and presses the button so the door closes. For the first time since they’ve gotten back together Dan doesn’t know what he should do next. It’s a given he needs to call her, but his call goes straight to voicemail. Does he go to the restaurant where she made the reservation? Does he wait for her to come back? Does he try to find her? He settles for some sort of combination of all of them and starts by sending a text.
7:49 PM - Dan to Blair
Please, come home.
He wants to tell her he loves her, but he hasn’t told her in person yet, and doing it now will definitely come across as a manipulation. Instead he goes downstairs and waits for her outside. Waits for her to come home.
He keeps his phone out in case she returns his call and then walks back and forth outside, not really pacing but it’s repetitive enough to irritate the doorman. He considers running inside to go get a coat when he sees her coming down the sidewalk, a cup of ice cream in her hand. It’s tempting to run and meet her halfway but if she sees him there and wants to turn around again, he wants her to be able to.
“Hey,” he says, when she’s close enough.
“I’m done with this,” she says in response, handing him her cup of ice cream. It’s chocolate chip cookie dough which is what Dan orders. Blair always makes fun of him, comparing him to a child with an unrefined palette. Which means she got this for him.
She walks into her building and Dan follows. They stand waiting for the elevator and Dan startles when Blair reaches for his hand, interlocking their fingers. He breathes easy for what feels like the first time since their stupid fight began. Except it must not have been stupid because something happened to really get to Blair.
Dan sits down next to Blair on a couch in her living room. He’s still stupidly holding the cup of ice cream but he doesn’t want to drop her hand to take care of it, so he sort of balances it on his knee.
Blair notices, because she notices everything. She takes the ice cream cup and sets it on a side table, and he knows she’s going to yell about rings on the wood later, but she’s not at the moment. Right now she’s playing with his hand — running a finger over his knuckles, comparing the size of their hands, interlocking their fingers, releasing them, then doing it all again. Eventually, she kisses his palm and cradles his hand in her lap.
“Towards the end of me and Chuck we stopped talking, really, but we still managed to find a way to fight. I would get upset and sometimes he would buy me something to make up for it. But other times I would be in the middle of explaining something and he would laugh at me and kiss me quiet. At first I thought it was romantic but then it felt like he was doing it because he just didn’t care what I had to say.” He squeezes her hand. “When we were fighting, and you kissed me, it felt like the same thing was happening. I don’t know. It’s a thing for me, I guess.”
“But you came back.”
“Because it was you,” she said.
At some point Blair stopped looking at him during her explanation so he gently tugs on her hand to bring her attention back to him.
“Blair,” he says. She looks back up at him and he smiles. “There are few things I know with more certainty than the fact I will always want to hear the sound of your voice.” He leans in with no intention of kissing her, simply rests his forehead against hers. He feels her shuddering breath pass over his lips.
“I promise.” He does kiss her then — a small tentative press of the lips. “Thank you for my ice cream.”
“You’re welcome. Though I hesitate to support your terrible taste.”
He ends up telling her he loves her the next day over breakfast. A small part of him is worried she’s going to respond as dismissively as she did all those years ago, but instead she leans forward, runs a hand through his hair and kisses him.
“I kinda had a feeling,” she says. She kisses him again. “And I love you too.”
“Yeah,” he says, smiling. “I kinda had a feeling.”
They’ve never had a formal conversation about the best way to handle it, but Dan and Blair choose not to ignore the reality of their messy and shared past. She doesn’t shy away from mentioning Chuck on the rare occasions they run into one another. Vanessa sends Dan an email that is somehow both blistering and complimentary after the publication of Almost Queen and he reads it to Blair over dinner.
“What am I going to do with you, Humphrey?” becomes a commonly used phrase in her vocabulary. Like when he shows up to her work event which she explicitly explained was “business casual” in jeans and a t-shirt and offers a passive “my business is being a writer, and this is me casual” as an explanation.
What am I going to do with you, Humphrey? It’s something she thought, and sometimes said, during their friendship and dating all those years ago. But he honestly mystified her most of the time. Now, though, it means something different. Most of the time all she wants to do with Dan Humphrey is be with him.
They’ve been together for a year and long distance for the entire span. There’s a wonderful simplicity to it all she still has a hard time believing in. She’s visiting him in Portland when she decides to maybe change that.
They’re lying on his couch (which she picked out because his was an abomination and she has a thing for couch sex and she wasn’t going to be naked on a thing when she didn’t know how old it was) and he’s dozing off. She’s kind of drumming her fingers against his bare chest, wondering what tack to take when she decides to just start talking. It’s a tactic she often refers to as the Dan Humphrey.
“I have a question.”
“It’s something I’ve wondered for a while.”
“Go for it.” It’s a sign of how far they’ve come that he doesn’t tense up in any way at her vague introduction. He’s just waiting for her.
“When we were in high school —?” She trails off purposefully. Blair kind of loves when Dan chases after her verbally.
He doesn’t disappoint. “When we were in high school, what?”
“Did you wax or did you shave?”
That startles a laugh out of him and he raises his head to look at her. She tries to hide her smile in his shoulder. “What?”
“You heard me.” She drums her fingers against his chest again, just to emphasize what she’s asking him. “Your chest.”
“What makes you —”
She huffs out a laugh at his indignant tone. “Please, you don’t think Serena shared every detail with me that year you dated? And, need I remind you, I interrupted you pre-coitus with Georgina?”
“No you did not need to remind me.” He sighs. “Wax. My dad did it, so I went to his guy.”
“Your dad had an esthetician? You were always more UES than I thought, Dan Humphrey.” He laughs and she settles back into his side. “But you don’t anymore?”
“Well, it hurts,” he says, simply.
“Yeah.” She runs a hand up his neck and then through his hair, tugging lightly on the roots so he’ll lean down and kiss her. Which he does.
“Your obsession with my hair borders on pathological.”
“I have another question.”
“It can’t be weirder than the one you just asked.”
“Do you want to live in Portland?”
“Forever?” She nods. “No, I don’t think so.”
“But you don’t want to live in New York?”
“I’m not against the idea.” He sighs. “I don’t know. I haven’t thought about it.”
“Haven’t thought about living somewhere else, or living in New York again?”
“Blair, what’s this about?”
She sighs and pushes off Dan’s chest to sit up. Dan follows her. She faces him and can’t help herself from running a finger along his jawline, feeling his 5 o’clock shadow. Maybe he’s right. She is a little pathological. “I got a job offer.”
She takes a breath and cups his jaw with her palm. “Come with me.”
He turns his face into her hand and places a kiss there. Dan’s eyes look sleepy and soft, and she knows what he’s going to say before he says it. “Okay.”
“Okay.” She kisses him. “God you’re easy,” she says.
He grins against her lips kissing her again and again. “You say the sweetest things.”