Wedding Date

Summery: Being single wasn't the worst thing in the word for Regina Mills, 31, creative designer, living in New York City. It had never really bothered her – much – but as her sisters wedding is fast approaching and her mother is constantly putting her down because of her old spinster status, she decides to bring someone – not being keen of being in the center of attention like every other time. OQ AU

A/N: so the general Idea for this fanfiction is based on the moving "wedding date" (hence the title) with Debra Messing. If you haven't seen it – you should. It's a great movie. I don't know how much I am considering the movie while writing that fanfic, maybe not much at all but the idea somehow stuck with me and I went along with it. Damn those plot bunnies that won't leave you alone ;) Also that of course means that this story is completely AU. No Magic and I made some changes along the line. Hope you still like it.

oh just a little headsup. this story will contain smut in the later chapters ;) so if you are not into this, you have been warned.

Also I do not own OUAT or its characters. If I did the season 3 finale had been hell of a lot different. ;)

Thanks to Darley for beta reading

Chapter1

„What do you mean you are coming alone? " Mary Margaret furiously yelled at her older sister "Why don't you bring that smoking hot boyfriend of yours. I´m sure he´ll look amazing in a suit" she added with a firm grin, that she knew her sister couldn't see but was sure that her voice gave it away.

"He is not my boyfriend" Regina answered with a soft sigh "He is a boy toy, a booty call and not even a good one. I was desperate okay? It's over now" she mentioned and Graham had really just been a substitute for a broken vibrator.

"Oh I am sorry to hear that. I thought he was a nice guy" the younger brunette told her sister with the innocent voice that sometimes reminded Regina of a fairytale character.

"The nicest. He told me we could fuck as long as we were both single." She replied and could practically see her little sister cringing on the other line.

"Don't be crude Regina; I am sure that's not what he said."

"I have the iMessage to prove it to you. After that he had the audacity to say he likes to cuddle afterwards - like that's supposed to be a bonus or something. As if I need that with a guy that comes after 5 minutes and then wants to know if he rocked my world!"

"Okay I am hanging up now sis. Just… maybe bring a friend or something. David and I would hate for you to be alone at our wedding."

"I´ll see what I can do" the sassy brunette answered before hanging up as well.

Sinking into the corner of the sofa, she propped her feet up on the low, wooden coffee table before her. Another soft sigh left her lips. Was it wrong of her to still believe in true love? That a guy could actually be interested in more than just her body? That dates actually made it to a second round. Her best friend Kathryn had nicknamed her "One date Gina" because she rarely got asked out a second time. If she slept with a guy on the first date, he never called again. If she didn't sleep with a guy on the first date, he never called again. It was like she was cursed. She knew there were decent guys out there. Her little sister had found one, after all.

David was a great guy; Good looking. Nice. Genuinely interested and the way his eyes sparkled when her sister walked into the room made Regina more than jealous. Still she was happy that her little sister was getting married to her own prince charming and she would be the best damn maid of honor she could be. With or without a date.

If she was quite honest with herself, she wanted this. The whole damn package. The guy that could listen to a boring story for hours, a man that could handle her sassy self, someone who put her into place when she needed it but worshipped the ground she walked on. Apparently though fairytale princes were rare and about to be sold out.

And it didn't help that Regina had hit the 30's mark. According to her mother, single women over 30 should just stop looking for a man and start looking for a couple cats.

A purring sound drew her out of her self pitying funk and brought her back to reality. She looked down at her lap, where her 8 month old kitten Nova had spread out. Okay, maybe she had listened to part of her mother's advice. That didn't mean she was ready to throw in the towel. The right guy was out there, she just had to be patient.

Her father Henry was different from her mother. He, like Regina believed that there was one person out there that you were destined to be with. On more than one occasion he had told Regina not to hurry it, that the one would eventually find her, that one day he would come knocking on her door, but by now Regina was wondering if "the one" was maybe not intelligent enough to find her freaking door.

Her fingers reached behind Novas ears and scratched. The little furrball purrs got louder. A cat was definitely not the worst, but, as much as she enjoyed her little toe-nipping she-devil, she wouldn't mind having a guy to cuddle up with. She let out another sigh. Damn it, there had to be someone out there, right?

"What do you say Kathryn? You and me, a nice little hometown wedding held in my parents back yard? Did I mention there will be free alcohol and some very delicious food?" she smiled brightly at the blonde that was currently situated opposite of her at the hell's kitchen restaurant. They had met up for a very late lunch considering Kathryn never took a break before 2.30 p.m.

"Oh honey, you know I would love to be your plus one, I would even like to give Cora my two cents about that cat advice, and while we are at it, I am still waiting for you to pay me back for the ruined Louboutins. But, I can't come. The office is hosting its annual benefit gala at the Ritz Carlton that weekend and I am presenting." She explained to her rather sad looking best friend.

"I hate you" Regina snapped back, joking of course and tried to drown her sorrows in the Long Island Ice Tea that the waitress just left at her table.

"No you don't," Kathryn laughed, her bright purple lips stretching into a smirk, "you love me." She snatched up her own drink and took a large gulp.

"You know… at first I even wanted to go alone" Regina whispered but before she could say more Kathryn's eyes had shot up

"You can't go alone; your mother would never let you hear the end of it!" To say Cora would be furious, would be the understatement of the year. Knowing her mother, she would even go so far as to say Regina had done it on purpose; to ruin Mary Margaret's wedding.

"You are right of course… which is why I asked youto go with me my dear"

"Oh because bringing your workaholic single best friend is any better?"

"Probably not, but at least you and me could have gotten gloriously drunk together" she winked at the blonde before the conversation came to a halt as their food was placed in front of them.

It was almost midnight and Regina had just fallen asleep (Nova snuggled up by her feet) when her cell phone rang loudly, making her groan.

Checking the caller ID she picked up with pursed lips "This better be important Kat, I was dreaming of Hugh Jackman – and he was naked." She added

On the other end of the line Kathryn chuckled. "Oh honey, if you need dreams like that to keep yourself going you're in worse shape than I thought!"

"Shut it dear. What do you want?" the brunette asked impatiently

"I might have a solution for your dilemma" her friend finally uttered out.

Regina sat up, her interest piqued. Please, oh please, oh please, have a viable solution, she silently pleaded. Aloud she asked, "you do?"

"I do"

Regina let out a sigh of relief. "Oh thank God! I was starting to think I might actually have to go to this thing alone. And really, the idea of facing my mother without a date..." she shuddered.

"Am I allowed to speak now or do you want to keep interrupting me?"

"Sorry. Go on please"

Well, I was talking to Emma about your...little problem" Regina groaned. "Oh shush, you don't have to like that I talked to her but for once she had a pretty good idea." A second groan followed the first. They had met 26 year old Emma Swan 2 years ago at a club where Emma had just started working. She had made them the best Long Island Iced Teas they had ever tasted. And, since it was her first night and they were her first customers, she didn't charge them. It was the start of a beautiful, if not sometimes annoying, friendship.

The trouble with Emma was she was always coming up with something, and she never had good ideas. Many ideas, yes, but most of those ended with jail time or an order to stay away from Macy's. Among other things. Still, she was fun to hang out with, and she made Regina and Kathryn feel younger. Plus, when they were hanging out with Emma, they were too busy trying not to get arrested or kicked out department stores to think about their lack of viable Mr. Rights

"I am sure I will regret my question, but what did Miss Swan suggest?" she wanted to know, biting down on her lower lip as she waited for the answer.

"She suggested a callboy" the blonde replied her voice deep and clear.

"Funny Kat, really funny. Not even Emma would go THAT far. So what did she really suggest?"

"A Callboy Regina. An escort service. Someone who accompanies you for money. A guy that will pretend to be your date." Kathryn tried again

"Oh my god you are serious, aren't you?"

"Dead serious"

"Holy shit. Is she dense? I can't call an escort service and bring a guy that I BOUGHT to meet my family."

"Then don't tell them" Kathryn said, not being phased at all

"You guys are crazy. I am not that desperate." Regina gave back

"Graham" the blonde coughed on the other line, chuckling softly

"That was different, everyone has stupid moments sometimes. But I am certainly not paying for a guy to entertain me. I have self respect."

"Oh and that's going to win you what exactly with your mother?" Kathryn asked, smirking to herself

"Touché" she sighed softly, trying to let that thought enter her mind. She couldn't really do this. Could she? A Callboy? Someone who was paid to smile politely at her and tell her that she looked pretty? Did she really have no other choice?

"I am sending you the link via email right now. Just check it out. If you don't find anything good, you don't have to do it. But Regina… the idea isn't the worst. I mean you would have someone to go with your to your sister's wedding and after that you could just send him packing and continue to live your life looking for Mr. Right. It can't hurt, can it?" the curly haired blonde whispered, knowing she was getting to Regina this way.

"I´ll think about it. Thanks for the brilliant solution" She sarcastically managed to reply before she hung up, falling back into the covers, her mind whirling.

TBC?

Okay this was the first chapter of Wedding Date. I was pretty hesitant about posting it since I havent written anything in a really long time and I am a bit rusty. Also English isnt my native language so bear with me please. Tell me what you think. Worth continuing? Would love to hear your opinions about this. Also if you have any suggestions or anything you would want to happen please let me know as well.