Actions

Work Header

Ten Night Stand

Chapter Text

“A hipster bar?” Regina couldn’t help the whine in her voice as she stood outside the bar looking up at the sign that sounded so hipster she rolled her eyes.

Regina Mills had a long, utterly exhausting day at work, and the last thing she wanted to do was meet her sister Zelena for a drink. A drink with her sister usually turned into a long drawn out ordeal at times, especially if Zelena fancied anyone at the bar. Regina wanted to go home, kick off her heels, finish off some emails, curl up with her favorite pasta dish and some wine while falling asleep watching a baking competition show. She took a deep breath and exhaled, feeling the stress of the day coil in her shoulders and neck. She needed to use her meditation phone app more.

The location of their drink had her perplexed, her sister usually preferred the posh places, dare one say snotty places, as Regina walked closer to the entrance she took back her first judgment of the establishment. The bar looked almost downright low key, which immediately charmed her. Regina would never let her sister know she preferred this type of bar than a more upscale one.

As she pushed open the doors, the warm air of the bar hit her, and so did the smell, a mixture of alcohol, sweat, and hipster. Regina scanned the bar and located Zelena sitting at a small table off to the side. Her red-headed sibling raised her glass and smiled.

She loved her sister, yet ever since Zelena had started working for their family company a few years ago, Regina’s blood pressure had gotten higher, and the workload more massive and chaotic. Thankfully, Zelena would go weeks without venturing in the office to wreak havoc, and this drink could go either way. Sometimes Regina wished she could fire her sister, but her parents wouldn’t allow it as silent partners at the firm. A quick drink was an easy fix instead of an all-day weekend gathering with a combo pairing of her sister and parents or some all night sister bonding sleepover.

“Why did you choose this dive bar?” asked Regina as she removed her blazer and swung it on the back of the chair. She looked more casual now in a silk blouse and skirt; the blazer added a fiercer element to the lady boss work ensemble.

“I thought it would be fun,” Zelena smiled brightly at Regina, and then stared hard, “you might even meet someone.” She raised her eyebrows suggestively to Regina.

“Meet someone here?” Regina looked around the packed bar; the crowd ranged from a wide variety of people, none that seemed that upscale for a change. It was a diverse mix, but that wasn’t going to stop Regina from teasing her sister and hopefully shut down any scheme brewing. “For what? Hire a killer? Contract a venereal disease? Learn how to bake cannabis edibles.” She raised her eyebrows in a match to her sister.

“There are a few people here I wouldn’t mind getting a venereal disease from,” Zelena’s eyes scanned the bar, stopping on quite a few of the hunkier men. “Or an enhanced brownie.”

“You’re incorrigible,” Regina snorted, she patted her sister’s arm. “Go get your baby sister a drink.” Regina became engrossed in reading emails on her phone as Zelena gave her an eye roll and trotted over to the bar.

On the other side of the bar at a larger table, a tall brunette with streaks of red in her hair sat with a blonde female couple as they were chatting happily until a taller, slightly older blonde dashed up out of breath and plopped down in a chair.

“Sorry, I’m late,” the blonde pulled off her leather jacket and draped over it over her chair.

The brunette eyed the blonde suspiciously, “Emma, you have that look.” She motioned her hands over Emma’s face.

One of the younger blondes spoke up, “She does! It’s THAT look.” She leaned into the other younger blonde woman and giggled.

“What look?” Emma squinted her eyes at her friends.

“Like you don’t want to face our judgment,” the brunette stared hard at Emma while she took a sip of her drink.

“Argh…” Emma dropped her head to the table “…Ruby…how do you always know?”

“She knows!” yelled one of the younger blondes too loud.

Emma lifted her head, scrunched up her face, and winced at the high pitch screeching of her already drunk friend then dropped her face to the table again. “How is Alice this drunk already?” Emma lifted her head again, reached over, and pulled Alice’s drink away from her. Then she dropped her head back on the table in defeat.

Ruby looked down at her friend’s head on the table and smirked.

“You’ve got like this sheepish walkabout you after you dump someone for a few hours.” Ruby rubbed Emma’s arm then moved to run her fingers through her hair since her head was taking up most of the table. “I know from personal experience.”

Emma groaned loudly from beneath her golden locks splayed across the table.

“Let’s get you a drink,” Ruby stood up and pulled Emma along with her, she continued to push her friend and ex to the bar.

Ruby noticed a stunning redhead by the bar; she maneuvered Emma so they could stand next to her as they waited for their chance to get the bartender’s attention to order more drinks.

Zelena noticed the two attractive women standing next to her; it was hard to miss them as the brunette one dragged the blonde, almost kicking and screaming to the bar. The blonde looked bratty and nearly wild in her tight jeans, knee-high boots, and a white tank top with a black bra visible underneath. A smirk grew wider across Zelena’s face. The two women started talking, so naturally, she leaned in so she could eavesdrop on their conversation.

“So…Lothario Swan, hunting for new prey tonight?” Ruby raised her eyebrows to Emma. “Should I warn all the women about you?”

“Ruby…please…” Emma shifted uncomfortably from one leg to another, “…it was only a one night stand. She knew that going in.”

Ruby let out a long dramatic, sigh yet with sadness in her eyes. “It’s always a one night stand with you, Emma.”

Zelena’s eyes grew wide, still listening to the two women; she pretended to ignore them when the dark-haired woman looked her way. The bartender arrived with her drinks, and she left the bar with a bored look on her face. Oh, she thought, I’m going to have some fun with Regina tonight.

Meanwhile, back at the bar, Emma ran her hands through her hair, waiting for a lecture from Ruby.

“You have let some amazing women slip through your fingers because of your commitment issues,” Ruby stopped and put her hand in front of Emma’s face. “Do not make some finger sex joke right now.”

Emma slumped her shoulders; it was such a perfect set up for a sex finger joke. She furrowed her brows, pursed her lips, and listened to her ex/close friend go on a long monologue on why she should give long term commitment a chance. Emma thought to herself for the same reason she didn’t have a car or house; anything could happen; something terrible could happen at any moment, and it’s going to hurt a whole lot worse if you have deeper attachments.

“Emma, seriously just try dating someone for longer than a week. I promise you it will be worth it,” Ruby tried hard to make eye contact with the male bartender.

“It’s not my thing Rubes…” Emma looked away and then sheepishly brought her eyes to stare at her friend, who yes she did dump a long time ago. “…as you know from personal experience. And before you start, it’s not about monogamy; I could’ve had sex with you for the rest of my life.”

Ruby turned her head so fast to gawk at her ex-lover with fire in her eyes. “Are you fucking kidding me, Swan. You’re the worst.” She slammed her hands down on the bar. Ruby admitted to herself, and it was probably evident on her face, that one stung. She always knew she liked Emma more than Emma liked her, yet they did have a great time together, so it took some time to get over the blonde.

Emma wrapped her arm around Ruby’s shoulder; she waved at the bartender and finally got his attention. She squeezed her hand and rubbed Ruby’s arm.

“Of course, he’s into blondes,” Ruby snapped, she tried unsuccessfully to shove off Emma’s arm. She took a deep breath and bit her lip. “So if it’s not about monogamy or sex, then why don’t you ever date anyone longer than like a hot second?” Ruby had asked this question before, but she felt the need to ask again.

Emma let out a long deep sigh. She didn’t know herself except that her lack of upbringing, moving from foster home to foster home prevented her from putting down roots. And instead of dreaming of one day of having a stable family, she had spent the rest of her life making sure that never happened.

Ruby got a wicked grin on her face as she looked back to Emma, and yes, she thought to herself, maybe she wanted a little revenge from the comment she just heard.

“Swan, you need to grow the fuck up.” She grabbed Emma’s arm from her shoulder; Ruby brought both hands to hold in front of them on the bar. “You’re going to take a bet.”

Emma’s eyes and mouth went wide gaping at her friend. She knew nothing good could come from betting with Ruby. They had a long messy history of betting against each other, then having big fights after and then long, uncomfortable periods of post bet angst. Emma was still sore after losing her beloved car to Ruby, okay, so she did have a car at one time. And she loved that car, and it hurt when she lost that car. She didn’t buy it though; she kind of stole it. However, that didn’t mean Ruby could take it from her.

“Ruby, we agreed for the sake of our friendship and sanity, no…more…bets…ever,” Emma said each word separately for more effect she hoped, and she gave her most serious stare.

Her dark red streaked friend continued to smile big. “I’ll bet you something you want that you can’t date someone for three months.”

Emma rolled her eyes. “I’m not taking that bet. There’s nothing I would want bad enough to date some rando for three months.” She looked at the cocky smirk on Ruby’s face.
“Yeah, you will,” Ruby licked her lips as her shit-eating grin spread across her face. She knew Emma would cave and take the bet.

The two friends were insanely competitive with each other. One time when they both got step trackers, they walked the entire length of the city before calling a draw and passing out at 4 am with blistered feet and dehydration. One time Ruby’s grandmother Granny asked the two of them to help out in her diner, and the women spent the entire night competing on who could get the most tips. The evening ended in many broken dishes, a black eye, and a broken jukebox that Granny never got an explanation or closure. When Robin and Alice announced they were getting married, Emma and Ruby bet who could throw the best bachelorette party. The party weekend extravaganzas ending up in massive hangovers, a broken nose, and another busted jukebox at Granny’s diner.

“You can’t bet anything that would make it worthwhile to me for that kind of drama,” the bartender finally dropped off their drinks, and Emma took a long swig of her beer.

“Your bug.” Ruby reached over for her glass as Emma was left choking on her recent swallow.

“What?” Emma grabbed a napkin to wipe up her mouth where she had choked, and her beer dribbled down her chin.

“I know you want your beloved bug back after you lost it to me. Here’s your chance,” Ruby smiled as she picked up her drink and walked back to their table.

Emma mumbled to herself, “Yeah, because that bet was completely unfair and stupid,” as she followed Ruby to join their friends.

When Zelena returned to her table, Regina engrossed on her phone didn't look up. She had such a wicked grin as she stared at her workaholic lovelorn sister. She decided to put her devious plan into action; her sister needed to get laid and not tied down by yet another loser — what better way than a cute blonde player woman.

“Regina, when was the last time you had a date?” Zelena appeared casual as her eyes found the commitment-phobe blonde across the room sitting at a table with the dark-haired beauty and two younger blonde women.

“I dated Robin for two years,” Regina said without looking up from her phone. “You know this.” She put down her phone and took a sip of her wine.

“No, that doesn’t count. I mean a date that didn’t lead anywhere,” Zelena’s eyes twinkled.

“What’s the point of that?” Regina squinted her eyes at her sister; Zelena was up to something. She had to make sure to stop drinking; she didn’t want to end up with another random tattoo.

“To have your eyes roll back into your head,” Regina stared at Zelena, utterly confused. “To get laid, dear sister.” She put her hand gently on Regina’s and patted it.

Regina rolled her eyes. “One night stands are not my thing Zelena.” She then tried to put some dramatic weight behind her words by staring intensely into her sister’s eyes. “I’m not a one night stand kind of person.”

“Well…become one. It would be fun for you and dare I say, good for you. Clear out your lady pipes.” Zelena took a long gulp of her frilly fruity drink. “You never dated casually, you always go into these ridiculous long boring engagements. I think you need to date around. Have some one night stands.” Her arm and hand gestures got big and mime like to the point where Regina tried getting her sister to sit back down properly in her chair.

“We have very different definitions of fun and health standards,” Regina sat back down in her chair and smoothed down her hair, which already looked flawless.

“Regina…dear dear sister…” Zelena pouted and puffed her lips out as she stared at Regina.

Regina rolled her eyes. She knew this was about to become pseudo serious, Zelena added an extra ‘dear’ to sister.

“Okay, if not a one night stand…what about a ten night stand?”

“What the hell is a ten night stand?” Regina scrunched up her face to her sister.

“Go out with someone for ten dates, then dump them, or if you get dumped by them before that, then even better!” Zelena had a big grin on her face, and her eyes were sparkling their bright blue color.

Regina stared at her sister, dumbfounded. She didn’t enjoy Zelena’s wacky ideas during meetings and not now either. Her sister’s plans rarely made sense to her or anyone else.

“A fling Regina,” now it was Zelena’s turn to roll her eyes at her sister. “Here, I’ll make it interesting and motivating for you. If you take my bet and win…”

Zelena then held Regina captive by pausing, a long pause as if she was a host on a reality show about to give results and kick someone off. Regina sat still and watched her sister closely.

“I’ll leave the company.”

Regina tilted her head, not that she didn’t love her sister, but working with her at their family company was torture most of the time. Her sister only caused drama and disruption when she was bored enough actually to work in the office, but most importantly, she was terrible at business and got them into horrible and costly situations.

“You can’t be serious,” Regina hoped that Zelena was serious. As Regina studied her sister, she let a loose deep chuckle escape her throat. It was a warm, rich laugh; one people always wanted to hear again and again.

Zelena leaned across the small table and stared intensely into her sister’s eyes. “Can you imagine how smoothly weekly meetings will run without me there? You won’t run out of your precious almond milk in the break room. No more additional harassment training courses because of me.”

The mere idea of Zelena leaving the company or at least becoming a silent partner was immensely appealing to Regina. So much so, she might be willing to take a silly, immature bet from her sister.

“I go on ten dates, and you leave the company? That’s it?” Regina was very skeptical; there was a crazy fine print she couldn’t see yet.

“That’s the bet, dear sister,” Zelena took a sip from her drink. “I pick someone right now for you to go on ten dates. Only ten dates, then it’s over. A fling Regina.”

And there is the crazy hard to read fine print, someone at THIS bar. Regina rolled her eyes and groaned.

“Someone from this place?” Regina looked as if she got hit in the face.

And now her internal debate started in her head to take the crazy bet or make the wise choice and don’t. Oh, she thought, she did want her sister to leave the company. She knew Zelena didn’t enjoy working at the family company, but she didn’t want to push her out either. Zelena was just stubborn enough to stay just to annoy Regina. The internal debate was over; she needed to win this bet and boot her sister out. Kicking Zelena out in a nice way, of course, with a generous severance package and glowing endorsements.

Zelena looked at her with mischievous eyes, “Yes, I’ll pick someone at random from this place, and you go on ten dates with them.” She knew exactly which ‘random’ person she was going to choose. She managed to hold down her smirk.

“Why ten dates?” Regina asked her sister with squinted eyes. She wanted to ask why this place but knew better to provoke her sister further.

“You said no one night stands. And for you, I would imagine this poor soul is only going to get to second base on the sixth or possibly the eighth date, but by maybe by the tenth date, you’ll get a decent shag or some heavy petting…” Zelena took a sip of her drink while she eyed her sister.

Regina pondered this ludicrous idea. “A ten night stand sounds like a plot from an insipid rom-com.”

“Don’t knock silly romcoms; we need them. Especially in the state of the world today,” Zelena pointed up to the tv monitor in the corner of the bar, displaying yet another catastrophe news event.

“Zelena you know I just can’t jump into sex, I need a connection,” Regina stared thoughtfully at her sister. “What if I can’t find that connection in just ten dates?”

“Yes, I forget you’re one of the types I can’t remember… sappysexual? Is that the brainy nerd sex one?” Zelena furrowed her brows as in deep mock concentration.

Regina wanted to smack her sister, okay yes, she wasn’t like most people. She couldn’t just jump into bed with someone. She did need a connection of some sort.

“Zelena, I don’t like labels.”

“Boringsexual? Demineorotic? Is that it?”

Zelena said the last part a little loud; a few nearby tables glanced their way. Regina could feel her cheeks warming.

“At least you’re bi thank gawd. Or are you pan? That would be wonderful.”

Regina lowered her head then decided she wasn’t going to let her sister embarrass her. She hadn’t dated a woman in a long time, not really since her serious relationship in college with Mal. Regina thought they might one day get married, but that didn’t happen. Sometimes it hurt too much to think of dating another woman, so she started dating men again.

Over across the room, another bet was about to take place, with two equally stubborn, competitive women.

“Don’t you want a chance to win back your beloved bug Emma?” Ruby teased her friend.

Emma squinted her eyes at Ruby. She did want her bug back; however, this bet was ludicrous even by Ruby’s standards.

“Ruby, this bet is just stupid. I don’t want to fake date, someone, for three months, that seems mean…” Emma did not like the idea of being forced to date someone, let alone for three months.

“Even for someone like you?”

“Ouch, that hurts Ruby,” Emma stared hard at Ruby. Okay, so she fucked over her friend one time, she did feel bad it didn’t work out between them.

“Fine. Listen, I’ll pick someone out, and you go on one date with them.” Ruby gave Emma a stern look, then put her hand on Emma’s arm and squeezed. “If you like them at all or at least want to fuck their brains out, then you gotta give it a go.”

“Classy,” Emma scoffed at her friend as Ruby let a little laugh escape from her lips.

Their two other friends at the table Robin and Alice watched on in amusement with a little disgust mixed in.

“Maybe the two of you should stop making insane bets with each other,” Robin said delicately in hopes of not setting off her two competitive friends.

Emma and Ruby both glared at Robin.

“Ruby, that bug is mine.” Emma thought she needed to state this fact again.

“Swan, you lost fair and square,” Ruby gave Emma her serious look then raised her eyebrows, “This is your chance to win her back.”

Emma groaned. She already hated this bet.

“This is such a lame bet. I have to date someone for three months?”

“Yes, you have to date the SAME person for three months.”

Emma wanted her yellow bug; she missed that car so much. She thought about the logistics of dating someone for three months. On the upside, work has been so busy Emma probably could only see the person once a week, so that might only be eight dates, as she did the math in her head. Another upside might be having sex for three months; regular sex could be very nice, she thought. She would have to pick the right person, though, for that to work.

“And I pick the person tonight. Here,” Ruby almost cackled to her friend’s shocked face.

“What? Why tonight? Why here?” Emma’s mouth fell open in shock.

Ruby didn’t have a plan, but she thought there were some people at the bar that would make ideal candidates to torture Emma for three long months. She did a once over at the gorgeous redhead standing next to her at the bar. The way the woman ordered a drink seemed obnoxious; the redhead would drive Emma crazy in three hours. Her eyes followed the redhead back to her table and saw her companion, and for some reason, she knew she had to pick the stunning brunette sitting there. For one, she thought, the brunette looked like a tight ass, literally and figuratively, which would drive Emma’s libido and nerves crazy even more than the redhead. Both women looked rich and businessy, which would also work. Since Emma was up and coming at work, she needed someone to match her ambition.

“Because that’s the bet Emma,” Ruby said without a crack in her voice and proud of herself. Ruby admitted to herself, she was going to love seeing her ex and friend tortured a bit throughout this bet.

Emma frantically scanned around the room, looking for any exes or people she knew, this had to be a setup. Why would Ruby pick tonight for this kind of bet? Why did it have to be someone in this bar? Oh please, she thought, don’t be someone from work.

“Do I at least get three passes?” Emma pleaded with Ruby. “C’mon Rubes, that’s only fair.”

Ruby kept a serious face even though she knew Emma would insist on something like this, so she had already picked out three people she knew the blonde would pass on.

“Fine, if you insist.”

Ruby nodded discreetly to a blonde over the in the corner; she knew Emma would find something wrong with the woman.

“Pass, she looks like that barista who always gets my coffee wrong,” Emma scrunched up her face.

Then she motioned to a darker blonde over by the pool table; a few guys were hanging around the woman.

“Pass…hard pass.”

“On what grounds?”

“She’s into dudes,” Emma pointed just as the woman pulled one of the guys by the shirt and started kissing him. “Or at least tonight.”

Damnit, Ruby couldn’t believe her queerdar had been off on that one.

“I get another pass,” Emma shot out with a smug look.

“Fine,” Ruby frantically scanned the room, she needed to land on that smoking hot tight ass brunette last. Thankfully, her eyes fell on a pixie cut dark-haired woman wearing a flower dress with a sweater over it reading a book on birds sitting in a booth. She nodded towards the lone woman for Emma to see.

“Super hard pass. She looks like someone’s mom,” Emma shook her head and took a sip of her drink.

“Okay, but you only have one last pass…let me see…” Ruby pretended to scar the bar once again, then slowly nodded her head to her target table. “Ohhh, there is someone I would approach if not for meeting my true love,” Ruby got a dopey look on her face as she thought of Dorothy. “The redhead over there at one of the small tables.”

Emma looked over slowly across the room to see the redhead sitting at a smaller table. The woman was beautiful, yet there was something about her that spooked Emma. She knew passing on the redhead meant she was Ruby’s mercy for the actual pick. Her eyes slid over to the other woman at the table. Whoa. Emma made her eyes dart away, or they would have stayed there and feasted on the brunette as if she was an all you can eat buffet. Plus, she wanted to seem as disinterested in the brunette as possible in hopes that maybe Ruby would pick her.

“Pass,” Emma turned in her chair to do a slow glance around the bar. “Looks like the bet is a draw, Ruby.”

Ruby fought down a smirk; she knew Emma would be tempted yet ultimately pass.

“Good try, Swan.” Ruby turned her head slowly, scanning the bar too, yet she knew precisely her target for Emma. “So it looks like the woman you’re be dating for three months is…” Ruby paused for dramatic effect and to annoy Emma further, “…the red head’s seatmate…the brunette.”

Emma swallowed hard. She didn’t think Ruby would pick the stunning brunette who seemed to exude elegance and grace despite sitting in a grungy bar eating peanuts and sipping a cold beer. She probably would have hit on the brunette for fun anyway, knowing the woman was out of her league. Emma thought to herself, dating the brunette for three months might not be so bad. And the sex could be phenomenal. However, she needed to reign in her hormones and think practically.

“Uh, that depends if she’s single and remotely interested at all.” Emma pointed her finger at Ruby. “I get another shot if your picks are married or not interested,” Emma subtly looked over to the brunette again, she felt her cheeks warm which was a good or bad sign depending on how she looked at the situation.

“Oh, I won’t need another pick,” Ruby smirked.

Meanwhile, at said table with the intended target and her sister.

“So dear sister, are you ready for your ten night stand?” Zelena wanted to make an addition to the bet; she might as well have fun at the blonde’s cost too. “You can’t date this person longer than ten dates, it must either shrivel and die out before the ten dates end, or you dump their ass.”

Regina scowled at her sister.

“However, I’m sure it won’t take ten dates because any woman will get bored with you on the first date when you don’t put out and just offer a handshake.” Zelena cackle a bit.

“Woman? You never said it had to be a woman?” Regina looked up quickly and met her sister’s eyes with her mouth wide open in surprise.

“Regina, please give men a break, you have the worst taste in men.”

Regina let out a deep, long sigh.

“Fine, date a man AND woman for ten dates.”

“Zelena, please. Work has been insanely busy; I don’t even have time to date at all, let alone two people on some silly bet you have concocted to amuse yourself.” And hopefully, give me some sanity back at work when I win this asinine bet.

“A man would be easier to lose after ten dates.” Zelena oblivious to Regina lost in her thoughts. “All you would have to do is cry after sex, announce on social media every day how much you love him and can’t live without him, or get a plant and animal together.”

“Too many romcoms…” Regina trailed off, eyeing her sister with furrowed brows.

“I’m not sure crying after sex with a woman is going to do the trick, unless you do that ugly crying, you do when you watch that family soap opera you’re addicted to. That crying will scare off anybody.”

Regina furrowed her brows further into a deep scowl. That family soap opera was a well-respected drama, and she did not ugly cry.

“On second thought, I’m not sure that would deter a woman, I think it might mean there was a deep emotional connection,” Zelena was lost in her imaginary relationship thoughts. “Instead, kiss really badly. Talk politics and religion ALL the time, opposite views of hers, of course.”

Zelena started to pretend to randomly glance and search around the bar, picking someone out as her eyes fell on them, just lingering enough to make her sister sweat hopefully. Regina scoffed at everyone she picked. She continued the charade of searching through the bar, squinting her eyes and finding the blonde sitting at a table with a small group of women.

Regina did a sweep of the bar and followed her sister’s eyes. She noticed a beautiful blonde sitting at one of the tables on the other side of the bar. A small chant started in her head, ‘Please, don’t pick the blonde. Please, don’t pick the blonde. Please, don’t pick the blonde.’ She didn’t want Zelena to pick that blonde.

Zelena bit her lower lip; she waited for the right moment to point out the blonde from the bar. “The blonde over there.”

Regina turned her head to take a look at the table Zelena was nodding towards, as discreetly as she could. She saw three blondes and one brunette at the table, so she hoped for a wrongful clarification. “Which blonde? There are three blondes at that table?”

“Regina, darling clearly, the two younger blondes are a couple. The older, more age-appropriate blonde.”

“Sounds like you’re saying I’m old.”

Zelena tilted her head and pursed her lips. “I only speak the truth. Although, seeing you date a millennial would be such delicious fun,” Zelena cackled while Regina rolled her eyes.

“Oh, c’mon Zelena,” Regina felt her stomach drop. She was disappointed in how whiny her voice sounded pleading to her sister.

“What? Since you dated one blonde, you’re never going to date another blonde?”

“You once said you were never dating another Aquarius.”

Zelena rolled her eyes, “I stand by that.”

Regina tried to look over to Emma without getting caught. “Why the blonde?”

“I like the aesthetics,” Zelena smirked to her sister. “My nieces and nephews will be gorgeous.” She winked to Regina. “Go on and talk to her, woo her, dear sister. Weave some kind of magic. You’ll need it to land a date with her.” She lifted her head and nodded towards Emma. “Go get your ten night stand.”

At Emma’s table, Ruby was watching her and holding down a chuckle. Thankfully, their two love bird friends Robin and Alice were too pre-occupied with each other to care about yet another silly bet between their friends.

“Oh, I forgot another part of the bet,” Ruby had a wicked grin on her face.

“Too late, Ruby, no amendments,” Emma stared fiercely at Ruby.

“This one is only going to help you,” Ruby smiled sweetly now, trying to hold back her wolfish grin. “You can’t have sex with her.”

Emma laughed loud and hard. “You can’t be serious? This is no longer a bet; it’s petty revenge.”

“Don’t flatter yourself, Swan. I’m doing you a favor. You always jump too fast into bed, try a different approach this time,” Ruby grabbed Emma’s hand and then said softly as she stared into her friend’s eyes. “I’m trying to help you, Swan.”

“You expect me to date, someone, for three months and not have sex? That’s not possible,” Emma looked way too smug.

“Because you’re so irresistible?” Ruby rolled her eyes. She hated to admit to herself that Emma was right, the blonde could be irresistible at times, and for a short period of time she had fallen for those charms on constant repeat. “Okay…at least wait through a handful of dates or a month.”

Ruby noticed Regina staring at Emma and smiled. “Damn Swan, I think you hooked your target.” This was going to be more fun than she thought if the brunette was already interested in Emma. “She’s the hottest woman in here.”

“What?” Emma asked in between gulps of her beer. Her nerves were getting to her a bit now, was she going to do this? Try and woo some random woman at a bar and hope she can date her for three months to get her yellow baby car back? Yes. Yes, she was. She wanted that car, it was hers, and this was easier than going to Judge Judy to fight her case.

Zelena pushed Regina up from her chair; she then kicked her foot to walk in the direction of the blonde.

At the same time, across the bar, “Emma, make it a little easier on her,” Ruby jabbed Emma in the ribs to get her friend up and to move.

“Geesh, Ruby,” Emma reached for her side in pain. Ruby kicked her foot next. “Fine, okay.” She stood up and started sauntering towards the beautiful brunette headed her way. She hoped she was headed her way, or this was going to be embarrassing. The brunette was stunning and then she noticed a scar on her lip, Emma gulped and felt her palms sweat. She told herself to play it cool, so okay, this might be the most attractive woman you’re ever approached, don’t do anything too silly. Be cool, she told herself again.

As Regina got closer to the blonde swaggering towards her, she felt her cheeks warm, and a trickle of sweat roll down her back. She hadn’t approached a woman in years and certainly not one as eye-catching as this blonde. Her jeans looked painted on; knee high boots looked like something out of a swashbuckler movie and a tank top showing her sculpted arms. Regina had never dated anyone like this woman, getting Zelena stuck in her head all she could think about was having sex with this almost female-like Errol Flynn, all the woman needed was a vest and sword. She had to reign in her libido; she shook her head, trying to calm herself. Damn Zelena.

Luckily, space opened up next to a wall in the bustling bar, thankfully in the middle of both tables. The two women came up to each other and stopped. They stared at each other, willing the other to go first. Then they both spoke at the same time.

“Hey.”

“Hello.”

It was extremely awkward for both women. So they decided to try again at the same time, once again delivering the same greeting to their combined annoyance.

“Hi.” “Hi.”

A duplicate greeting on top of each other again felt even more awkward the second time, if that was possible.

Emma felt a trickle of sweat roll down her back. Get it together Swan, do you want to stick it to Ruby and get your car back? Swan up and get in wooing mode, she told herself.

Regina thought this was one of the worst introductions. What does this blonde woman do for work? She’s certainly not working with clients or greeting people.

“Regina,” she decided to stop the insane cycle, but she couldn’t figure out if a handshake was proper. It seemed a bit odd in terms of possible dating; this wasn’t a business transaction, so she nodded to the blonde instead. Although, perhaps thinking of this as a business transaction would be best to achieve her goal of short term dating and booting her sister from the company.

“Emma Swan,” Emma nodded to Regina and smiled.

“Ridiculous,” the word slipped from Regina’s mouth without precaution. The woman’s name even sounded like a swashbuckler Regina thought.

“Uh, thanks,” Emma replied with a snarky tone as she ran her hand behind her neck. This brunette had thrown her off her game already. Most people thought her name was cute.

“I meant your name,” Regina gritted her teeth, what kind of name was Swan? Utterly ridiculous, she thought, a silly daredevil swashbuckler.

“Yeah, I got that. What’s your last name? Poshington or Smithsonian?” This woman might not be an ideal candidate to date for three months. She was already too high maintenance for Emma’s tastes. Damn Ruby.

“No, it’s Mills,” Regina said proudly as a peacock puffing out all their feathers. “Mills is a classic name with a tapestry of history.”

Tapestry? Who uses a word like that in a sentence like that Emma wondered. “It also means…grinding. Are you a grinder?” Emma tilted her head and smirked. As annoying as the uppity woman was, Emma’s mind couldn’t help but wander below her waist and grinding of a different kind. The woman was attractive, but the air of superiority around her was unattractive.

Regina wanted to knock the smug smirk off the blonde’s face. This woman was distasteful from the red pleather jacket she could see slung over her chair back at her table to the scuffed worn boots she was wearing and the tight jeans she had painted. Regina was furious with her sister for saddling her with this tacky choice. She knew her sister must have known this blonde somehow and picked her on purpose to win this insane wager.

“The Swan family name means just a bird I’m assuming. A bird that carries a variety of diseases.” Regina narrowed her eyes at the blonde.

Emma decided if she would have some fun with the uppity woman. “Mills and Swan…has a nice ring to it. It sounds like we should start a detective agency.” Emma leaned in a bit, putting her arm against the wall to stare more closely at this Regina. “You look like you could pass for a film noir femme fatale.”

“I don’t think that would be a very successful endeavor. I would imagine you would eat a lot of donuts while I did all the leg work,” Regina was thankful she brought over her drink so she could take a sip while she eyed this Emma. “Plus, I don’t think you have the…style for it…pleather is a tad classless.”

Emma thought to herself, while the woman was astute, she did love donuts and pleather; and would love to see this woman’s legs work. Emma realized that she probably did not want to date this woman for three long months. This Regina Mills woman already seemed kind of rude and hard to talk to. She had to get Ruby to pick someone else. Having to endure a three-month charade with this arrogant woman would be an extreme gauntlet she didn’t think she could finish, she thought of her hero Xena and how even the warrior princess would fail this one.

“Some people would say classless is fun and classic is stuffy,” Emma crossed her arms against her chest.

“Yes, those are the same people who eat with their mouths open,” Regina glared at Emma.

Regina also realized, ten dates with this woman would be pretty tedious even despite the wavy long curls her hands wanted to run their fingers through while spooning. Damn her body for betraying her. She knew she wouldn’t be able to convince Zelena to pick someone else. She had to leave this bar either with this woman or firm plans to meet for a first date.

Emma had no idea what else to say to this woman; her brain just turned off in a way it hadn’t before. Her body did not; it was as if her body knew something her brain wasn’t aware of, and that worried her. She decided right then, she would force Ruby to pick someone else, and Emma was reasonably confident she could convince her. And if not, she could steal her car back or come up with another embarrassing bet that Ruby couldn’t refuse. It was decided in her mind, even though it was a brief meeting, she was calling quits on this snotty brunette.

“Well, I’ve got some donuts and pleather…” Emma trailed off, not knowing where her comeback was going, so she decided to cut it short, “…enjoy your evening…uhhh interesting meeting you.” Emma gave one last look over to this Regina; the woman was breathtaking; she begrudgingly admitted as she turned to leave.

Regina’s mind started to race; she couldn’t lose this bet; she desperately wanted Zelena gone from the company, and if this was the only way, so be it. Either she could turn on the charm, although Emma felt like she already tried that or be honest with this woman and see if she could strike up a deal without letting Zelena find out. She reached out and took hold of the blonde’s arm, her fingers brushing Emma’s soft skin and firm bicep. Emma turned around, surprised to see Regina holding onto her arm.

Brown eyes stared into green eyes. Regina took a deep breath, glanced down at her favorite heels, and decided to see where honestly would get her. It was not her best tactic in business, then yet sometimes it did work to varying degrees.

“Wait…” she brought up her eyes again to stare into Emma’s wide eyes, “…my sister bet me…” Regina found it hard to say out loud because it made her sound weak and unattractive, yet she forged on despite her eyes dropping to her shoes again, “…that I couldn’t get a date tonight.” Regina raised her eyes to stare back at Emma; she held her breath, waiting for a response.

Whoa. Emma was extremely surprised, another bet. What are the odds tonight of all nights, and in this bar, Emma wondered. What rom-com hell is this? Or luck? This Regina woman took bets? This fancy-ass snooty woman engaged in juvenile wagers? Despite Regina being hard to talk to and uppity, how could the woman have trouble getting dates? Emma realized she had to stop asking herself so many questions. She wondered if she should tell Regina of her bet. Then she thought about what she would do in a business deal; she would not divulge information that vital while closing a deal.

“You gotta get a date tonight with someone here to win a bet?” Emma narrowed her eyes and stared intensely at Regina.

“Yes, …actually ten dates,” Regina bit her lower lip.

Emma was a little transfixed by Regina biting her lower lip, okay that did something to her insides despite first impressions. “Ten dates with ten people?” What kind of crazy bet was this? “What number am I?”

“No, ten dates with one person. My sister is a bit mad at times,” Regina ran her fingers through her hair, she could tell Emma was watching her confused; the blonde had a dopey look on her face. Then thankfully, the confusion turned possibly into intrigue so that she might win Zelena’s bet after all.

“So you want ten dates with…me?” Emma’s eyebrows shot up in surprise. Oh, I could use this to win Ruby’s bet, after all, she thought. She realized she could stretch ten dates to three months easy.

“Yes, it can be a formal agreement between us. It would just be a show for my egomaniac sister…as long as she never knows…that you know…or we know together.” Regina shook her head; she sounded like a bubbling idiot. Or plot thread from Friends.

“Ah, the old fake dating…” Emma gave Regina a wink. “You didn’t strike me a rom-com nerd.”

Regina scoffed at the blonde’s crazy wink. “Fake dating? This is not some idiotic rom-com trope,” now she was wondering if this blonde was in cohorts with her sister. She took a deep breath. “No. Okay…this is real dating…” She realized her voice wavered, and it almost went up as if asking a question, she wondered, was this fake dating? She wouldn’t have picked this woman to date at all; she was Zelena’s choice or punishment.

“Okay…” Emma leaned in closer, putting on her most charming smile. “You’re asking me out on ten dates? Ten real not fake dates?” This still didn’t feel like a real offer, Emma thought.

Regina knew she was going to regret this; she took a deep breath, hoping to calm her nerves and the desire to murder her sister. “Yes. Dating…what all that entails…activities…outings…sex…” Regina said ‘sex’ quieter than the other parts, and she hated she felt her face grow warm. She was not thinking of having sex right now with this beautiful yet irritating blonde in front of her.

Emma stood momentarily, stunned for a moment. She had never been asked out in quite this way before. Sex. Huh, she usually would jump on the sex part, but she had played down that part because of Ruby’s stupid, cruel addition to the bet. She didn’t know how to respond to this proposal, despite that it could help her immensely.

Regina waited for this Emma to respond. She got nervous with the prolonged silence; she should not have mentioned sex. She paused for a moment; maybe fake dating was better than real dating if this insane person was up for it. “…I thought we could date...without an agenda.”

“Doesn’t all dating have an agenda?” Emma lifted her eyes to start at Regina, asking the question.

Regina squirmed a little; she could always feel when she was about to close a deal. She had no idea right now if she was close or not with this, Emma.

“You must want something pretty bad to win,” Emma smiled at Regina; she knew the feeling. Did this woman also want her beloved car back? What did this woman want to win over her sister?

“I do. And my older sister usually gets her way, so it would be nice to beat her for once,” it was the first sort of sincere thing Regina had said since she started talking to this Emma.

“This could work,” Emma started thinking, this could work to get her yellow baby car back. This woman wanted to win her bet just as much if they joined forces they could both win.

“What could work?” Regina furrowed her brows and looked at Emma for an answer to what seemed like a riddle.

“Nothing, let’s get out some basic info out of the way…are you attached?” Emma leaned in more interested now, invading Regina’s personal space. She noticed the brunette smelled too good; she inhaled again to get another hit.

“Unattached,” Regina shot back to Emma, “You?”

“Single. Are you psycho?” Emma tilted her head and raised her eyebrows.

Regina scoffed. “I’m passionate…if there is a good cause.”

Emma thought that probably translated to possibly unhinged if something went amiss or didn’t go the uppity woman’s way, dully noted that could cause problems after the three months when she needed to dump the woman.

“Where are you on the…sexual spectrum? I’m assuming since you’re asking me out on ten dates, you’re at least bi.” Emma’s eyes glanced down to Regina’s lips then back up to her eyes.

Regina rolled her eyes and grumbled, “I’m not asking you out on ten dates.” Since she had caught this blonde staring at her lips she decided to stare at Emma's mouth; she licked her lips.

Emma raised her eyebrows; she stood so close to Regina; their bodies were nearly flush up against each other. She wanted to move closer, Regina smelled utterly enticing.

“Then, what are you doing? It sounded like you wanted me to go on ten dates with you.” She could have some fun with this uppity woman and get her car back; this might not be such a bad three months.

Regina realized they were standing so close together she could feel the heat coming off Emma’s body. She decided to take her chance on a hutch. “No one is forcing you to go on ten dates with me. Take it or leave it.” She turned to walk away from Emma, this time, it was her turn to make a fake exit.

And this time it was Emma’s hand reaching out and wrapping around Regina’s wrist. She couldn’t let this woman get away; this was a great match for getting her car back and winning over Ruby. “Alright, deal, lady. Ten dates.” Emma dropped Regina’s wrist when she realized her thumb was unconsciously rubbing the smooth, warm skin.

“Meet me by the door,” Regina turned abruptly and headed back to her table with a smirk on her face. She was happy being able to flee the bar and her sister while it was still relatively early, she could get some work done at home.

Zelena looked surprised as Regina strolled over and picked up her jacket, phone, and purse. “Where are you going?”

“I’ve accomplished the start of your bet, I’m going on a date with that blonde woman you picked out,” Regina smoothed down her shirt, ran her head through her hair and took one last sip of her neglected drink.

Zelena had a wicked grin on her face, “Dear sister, if you truly have a one-night stand tonight, I’ll leave the company immediately and pay back all the harassment lawyers.”

Regina knew that lying wasn’t the way to win this bet. “She’s just escorting me home; we have a date next week.”

“There is the Regina that I know and sometimes tolerate,” Zelena beamed up at Regina. “Have a good evening, dear sis, and if the urge hits…just jump her bones and make her moan.” She winked and raised her glass as Regina turned and headed towards the door.

Over across the bar, Emma hurried over and grabbed Ruby’s new beer and drank most of it. She heard a growl as she grabbed her jacket and smiled at her friends.

Ruby gave Emma a side-eye, “Just remember Swan, you can land her tonight, but you gotta keep landing her for three loooooong months.”

“You might as well hand over the keys now, Ruby,” Emma gave a smug grin to Ruby then pointed to Robin at the table. “Robin, you’re the only sober one, make sure they both get home okay.”

“Text me later, Swanova,” Ruby giggled at her own silly name.

Emma turned quickly to glare at Ruby with her hair bouncing on her shoulders. She turned back around to almost collide with Regina by the door. They both took in a deep breath.
“Are you ready to leave…Ms…Swan?” Regina noticed how ridiculous the name sounded on her tongue, yet also somehow not out of place with regards to the blonde.

“We’re starting our first date now?” Emma’s eyes widened as she followed Regina out of the bar’s main entrance.

When they were safely outside, and of our earshot of one crafty, wicked sister, Regina said softly to Emma, “No, let’s meet next week for date one.”

As she finished her sentence, a car service pulled up, and Regina opened the door for Emma to enter the vehicle, “I’ll drop you off.”

“Uh, thanks,” Emma looked confused as she climbed into the car. She scooted over across the seat to make room for Regina. Emma pulled up on her coat as Regina got into the car and sat beside her. They bumped into each other as they put on their seat belts.

As soon as the car was moving, Regina studied her phone, and Emma sat there a little awkwardly. The first date next week, this was great news. Emma hoped she could string out these ten dates to three months.

“So when do you want to go out?” Emma watched Regina engrossed in her phone, the woman was stunning, and she felt her body react to her. Her traitorous body had been responding to Regina since she first laid eyes on her.

“What’s your email address? Might as well get your phone number…” Regina looked up and stared at Emma, “…but don’t text me all the time and certainly not silly things like a cat knocking something over or a baby burping. Or political stuff.”

Emma rolled her eyes; she wondered how this woman made hysterical memes sound unappealing. “Got it, text all hours of the night with lewd content only.” She stared at Regina, who returned a cold glare. “Here, give me your phone,” Emma reached out to take Regina’s phone, their fingers brushed against each other before the brunette finally relinquished her device. “Don’t worry; you’re getting it back unscathed.”

Regina watched while Emma put in her information into her phone. She bristled at the way the blonde just took her phone. Nobody took her phone; her phone was essential and very private. She could be getting sensitive emails, texts, or calls any minute from work. Regina felt her breathing getting shallow and her pulse quicken, she needed her phone back. She also realized she might be too attached to her phone; she needed to browse the meditation app for a lesson on letting go of your phone for five minutes.

“I have a huge project going on at work…” Regina picked at nails while Emma furrowed her brows and quickly typed in her information into the device, “…and I need my phone back…I don’t have time for dating…but my sister is the most odious woman in the world and…” she knew she had to stop her mouth from nervous talking. She looked up to see Emma staring at her and giving her phone back with a smirk. “Thank you,” Regina replied quietly.

The car pulled up to a stop, Emma reached over and patted Regina’s thigh. She gritted her teeth for reaching out and touching her, stupid hand betraying her.

“Thanks for the ride…I’ll see you next week, right?” Emma felt her cheeks warm; she didn’t mean to sound kind of clingy or unsure. She shook her head, that wasn’t her style. Something was unnerving about this Regina woman. Regina rambled in the car, too; it seemed the anxiety of their situation caught up to both of them. She almost feared what the first date would feel like or if they would make it through.

“Yes, I’ll email you soon,” Regina nodded to Emma. She reached out to shake her hand, then retreated, thinking of her sister’s snide comment.

“I’ll text you back,” Emma smirked to Regina.

Emma took that as her cue to shut the car door. She stood and watched the car disappear down the street. She didn’t know if she could date that woman for three long months, but she smelled good enough to try.

As Regina sat back in her seat, she looked at her phone. It appeared while Emma had her phone that she texted herself a gif of two cats ringing bells for treats. Going on ten dates with that woman was going to be trying, at least the woman was attractive and appeared to like animals.