This is very AU. VERY AU. I borrowed the basic plot from the movie "the Wedding Date". There will be things that differ from the plot of the movie though, and some things will be a lot different.

I'm really not that sure about posting this, but I kinda like how it turned out, so I figured I'd give it a try :) Please let me know what you think of it!

Disclaimer: I don't own Gossip Girl or the Wedding Date.

This is un-beta'd, I apologize in advance for any mistakes

Slamming the door of her cobalt blue Mercedes shut, Blair couldn't hold back a smile when she heard the distinct sound of the power door lock. The car had been her way of treating herself to something special in celebration of her promotion six months prior. It was classy and feminine and she had fallen in love with it the first time she saw it.

The sound of her heels echoed on the street as she walked across the sidewalk and up the front stairs of her Potrero Hill home. She had bought the hillside villa during her first week in San Francisco, having decided that if she really was to live outside of Manhattan, she would live in style. Blair Waldorf, fashion editor of the most popular fashion magazines in California, and one of the best-selling in the whole country, doesn't do things half-heartedly. Two years with the publication house and she had already seen the magazine change from being a decent selling publication to the must-read for any 18-35 year-old woman with an interest in fashion and styling.

The sound of her keys as she unlocked her front door also had a smile lacing her features. She adored her beautiful home, her own personal sanctuary. God knows she could use the peace and quiet after the day that she had had. Today had involved drama that far exceeded the acceptable quota. Paul, the latest guy in the group of well-educated, successful and charming men she had made a habit out of wining and dining - but nothing more than wining and dining, she's not some cheap skank, thank you very much - had turned out to be quite the disappointment. He had actually been stupid enough to believe that Blair dating other men somehow entitled him to see other women too.

A civil break-up from their non-relationship had been necessary, she mused, while she kicked off her Manolos and dropped her keys in the pale pink, glass bowl on the dresser next to the door. Too bad the poor bastard didn't handle punches to his ego very well. Was there ever reason enough to cause a scene in the middle of a crowded restaurant? The memory of her lunch date put a frown on her face. If there was, it was beyond her imagination.

She let out a content sigh as her tired and aching feet touched the plush rug covering the floor of the hallway. She picked up her bag from where she had dropped it on the floor and walked down the hallway leading down to her kitchen. This rare occasion, a night without having to attend a work event and without a dinner date, was going to be her excuse to spoil herself with a glass of wine, a bubble bath and a movie.

As she made her way over to the fridge to get some water, she pressed the button of her answering machine absentmindedly. The electronic voice indicating that she had one new message caught her attention as she opened the stainless steel door of the fridge.

"Blair". Oh joy, it was her mother. "Would it kill you to answer your phone? Really, in this day and age people really should be able to get a hold of you during the day, don't you think?"

She made a tired eye roll at the device, allowing the childish display now that her mother was not around to reprimand her on her antics. What on earth could be so important that it required Eleanor Waldorf to pick up the phone and call her one and only daughter?

"Anyway," The recorded voice of her mother continued, "I wanted to talk to you about the wedding," The wedding. A tight lump began forming in her chest. So that was the reason. "I do trust you to remember that it is no longer than a week left, and your invitation says 'plus one'. I know because I had lunch with Anne the other day. Now, I do expect you to bring someone respectable, Blair," her mother went on, and sounded like the idea of her daughter's personal life was cause enough for Eleanor to age prematurely. "It is bad enough to have to sit through a lunch with the woman, having to listen to her ranting about flowers and caterers, when I have to worry about you showing up to this nuisance of a wedding without a date. It would simply be unacceptable of you to show up unescorted, Blair. What would people say after all that has been going on between our families? Call me back."

The lump in lodged in her chest grew bigger by every word her mother added to the self-pitying rant. She had almost forgotten about the wedding. Or rather, she had done her very best to erase it completely from her mind, and had shoved the fancy, eggshell-colored invitation inside the depths of her enormous day planner. She rummaged through her red, patent Birkin. A few seconds of searching and she had found what she had been looking for. With a grim expression on her face she pulled out the invitation she considered to be every deity in the world's way to punish her for whatever it was they held her responsible for. The holocaust perhaps, or maybe global warming. She must have done something truly horrible to deserve this.

Mr. and Mrs. Andrew Lifton
Mr. and Mrs. Archibald
invite you to share in the joy
of the marriage uniting their children
Poppy Rebecca
Nathaniel Fitzwilliam

Nate. The mere thought of Nate entering into holy matrimony with Poppy Lifton was enough to make her feel queasy. She really, really wished that Poppy was the sole reason of her body's reaction, but sadly that was not the case.

She and Nate's relationship had been like something out of a fairytale. They met in kindergarten, became friends and then dated all the way through Junior High and High School. The King and Queen of Constance & St Jude's, and the Upper East Side too. She had been the Ice Queen with her court of loyal (terrified) minions, and he had been the charming and friendly captain of the lacrosse team. Yale followed after their graduation from High School, three years of blissfully making their way towards their happily ever after. Nate had proposed to her the night they both graduated from Yale. She accepted immediately, and they moved back to the Upper East Side. With Nate working at the New York mayor's office, and her with a new position at American Elle, her perfect life had been en route.

She had divided her time between her work and planning the wedding of the year. The latter definitely a more exciting pass-time in her opinion at the time. Perhaps she would have caught up with the signs earlier, had she not been so preoccupied with channeling a bridezilla in the making. If she had stopped to breathe every now and then, then maybe she would have noticed that something was not right. Then she might have been able to avoid the utter and complete humiliation of finding herself left at the altar on her wedding day.

Too much, too soon, not ready. Nate's excuses had been many once they sat down to have a 'civil and grown-up conversation about this utter disaster' as her mother had put it. All she can remember feeling is betrayal and humiliation. But instead of yelling or crying she smiled an understanding and patient smile, and told Nate that 'yes, she did understand where he was coming from, no hard feelings. Asia does sound amazing this time of year, don't worry I will handle the details'. Trivial details such as returning their wedding gifts and handling the media.

When a postcard from Singapore landed in Serena's mailbox two months later, telling her best friend all about Nate's travels and his new travel companions that he had met in Thailand, their old friends Poppy and Carter, Blair's gut had told her something was up. When Nate returned three weeks after the arrival of his postcard, joined by a deliriously happy Poppy, the later wearing a huge diamond on her left ring finger, Blair had been proven right and swiftly demanded to be transferred far away from New York and the Upper East Side.

A clear, lone drop landed on the paper in her hand, and interrupted her painful trip down memory lane. Suddenly dumping Paul over a Caesar Salad and a glass of sparkling mineral water didn't feel like the greatest idea of her 26 year-old life. So what if Paul was a complete bore and unable to keep his hands on one woman at a time? He was also a prominent lawyer, had good table manners and was quite the expert on excruciatingly boring small talk. He could be her plus one to the wedding; maybe she should give him a call tomorrow?

Oh no, no way, she decided and wiped the evidence of weakness off her cheeks, before stuffing the invitation back in her bag, she would not go there. No more Nate-inflicted self-pity or regrets. Though suddenly the prospect of a quiet night at home with her thoughts didn't sound as appealing as it had thirty minutes ago. No, she decided, walking over to the cupboard to find the Chardonnay she had been saving for a special occasion. Blair Waldorf doesn't mope or sulk alone on her chamber on a Friday night. Blair Waldorf, successful editor and gorgeous single woman, goes out on a Friday night. If a hot single woman can decide to go drinking in a bar alone, then perhaps hot, rich men might come up with a similar idea? (She really needs to find herself a date for that stupid wedding.)


"Stupid medieval-esque town," Blair mumbled under her breath as she walked down the road on her way home again hours later. Several hours, and several cocktails later too in all honesty. Sadly it seemed like most hot, single men took their soon-to-be-not-single dates to bars on Fridays.

"The lack of cabs in this town is simply," A hiccup escaped her lips, and she covered her mouth in horror from her plebeian display, only to burst into a fit of giggles the next second. "Unacceptable." She finished later on, in very best impersonation of Eleanor's disapproving sneer. Her own voice had her laughing again and she stumbled to the side, nearly falling over.

"Come on, Waldorf." She muttered, "Get yourself together and climb, that, hill."

Ten minutes later Blair was exhausted and annoyed. She sent her Manolos a patented Blair Waldorf death glare. Clearly her beautiful plum-colored shoes didn't return her love and affection. Judging from the blisters forming on the back of her heels, the pair of designer shoes was out to get her. She let out a huff, and ungracefully slumped down on the stairs of an old building, resting her elbows on her knees and cradling her head in her hands.

"Just a moments rest, and then you'll get going again. Alright, Waldorf?" She told herself quietly, intrigued by the discovery that the steps seemed to be moving like the ocean down in San Francisco Bay.

Blair didn't hear the sound of the door above the flight of stairs being closed, or the sound of footsteps descending to her level. She didn't become aware of the fact that she had company, until a pair of man's dress shoes showed up in her line of vision. The discovery indicating that someone, and a man with great taste at that, was standing right in front of her.

"You alright there?" A rich, velvet voice inquired. Realizing she was staring dumbfounded at the voice's shoes, Blair slowly diverted her gaze from the ground and looked in the direction which the voice was coming from, her upper body tilting a little to the side as she did.

Dark eyes were the first that she noticed, apart from the nice, tan-colored shoes. Dark eyes looking down on her, flashing with amusement and a hint of concern. She found herself mesmerized by those eyes, unable to stop staring. Then the dark-eyed stranger's lips tugged into something that could only be described as a smirk. A devilishly handsome smirk.

"Miss?" The dark-eyed, smirking, man asked her again.


"You okay?" The man questioned, "You look like you might need a hand."

"No!" Blair objected hastily, and began to push herself up from her position on the stairs. Suddenly feeling a little intimidated by her somewhat compromising position, sitting down on the stairs in front of a complete stranger. "I don't need he-" She almost made it to a standing position but the ground decided to take up its ocean-impression once more. She stumbled helplessly to the side and nearly fell over.

Before she barely had time to let out the undignified, shocked yelp that was escaping her lips, she found herself safely held in strong arms. He smelled of expensive cologne and cigarettes, she realized, and had to stop herself before she nuzzled into the fabric of his pale, grey shirt to inhale the for some reason intoxicating scent. The crisp cotton of his shirt the same color as the sky on a cloudy day.

He was holding her steadily by the arms while she struggled to regain her composure, and some of her pride. Finally succeeding she took a step back, smoothing out some invisible crinkles in her navy, silk dress. When she looked back at him again, she found the humored smirk still on his lips.

"You sure about that?" He smirked, cocking an eyebrow in her direction. She straightened her back further and raised her chin haughtily, narrowing her eyes. Who did he think he was anyway? Prince Charming?

"Just thought you might like a ride," The man continued, nodding to a black sports car parked by the side of the street. "There is always room in my carriage for a damsel in distress."

Was he gorgeous and a psychic? Didn't she just think about him in fairytale terms?

"I'm not a serial murderer or some crazy stalker; I just thought you might like a lift up the hill. I'm assuming that is the direction you're headed since you felt the need for a breather, " the man continued.

He had dark hair too, she noticed then, but his eyes weren't as dark as she had previously thought. Now that she was standing up and facing him in the light of the street lamp, his eyes had the color of dark whiskey.

"Like there is any other way to go than 'up the hill' in this godforsaken, ski slope of a town." She replied, and to her surprise and satisfaction he let out a deep chuckle at her remark.

"I take it you're not from around here then." He replied, and smirked at the obviously inebriated brunette in front of him. The shoulder strap of her navy dress had fell off her slender shoulder, and her dark curls were in disarray. She was gorgeous. The appalled look on her face had him letting out another barely contained laugh.

"I most definitely am not!" The brunette exclaimed haughtily, "I'm from Manhattan."

"As in New York?"

"Well of course as in New York! Is there another Manhattan just lying around somewhere nearby?"

"Haven't heard anyone refer to themselves as being from Manhattan before that's all," he replied calmly, discretely evaluating her. Inebriated, definitely, and a little upset about something too, he could see that in her eyes. But also most likely wealthy giving the pricey heels and the expensive designer dress. Actually, her whole air and appearance oozed with class and old money. Not the kind of class that came with being born with a silver spoon in your mouth, or channeling 'the talented Mr. Ripley'. No, this silky-skinned, petite brunette in front of him carried herself like an old Hollywood movie star. Or would carry herself that way, had she not been completely drunk and almost on the verge of falling asleep while standing up.

"Now, let's get you to the top that hill." He stated, and offered her his arm in an image of the perfect gentleman. He had been on his way home, but he was in a generous mood from the hefty tip he had received a few minutes ago.

"Fine." She sighed, and decided that she might as well take him up on his offer, linking her arm with his. "Who are you anyway?"

"I'm Chuck Bass." Chuck replied, and nothing in the world could have prepared him for her reaction. She broke out laughing. She laughed so hard she had to bend over and clutch her stomach.

"Your name," Blair choked out through fits of laughter, "Is Chuck Bass?"

A spear of ice shot through his stomach, but dissolved when she went on;

"What were your parents thinking?" She laughed. Trying to regain her composure she wiped tears off her cheeks and brushed some stray curls out of her face. "Having a surname that rhymes with ass, and then a first name that rhymes with-" She stopped midsentence, and was that a blush he caught coloring her cheeks?

"Rhymes with what?" Chuck taunted her amicably as they walked around his car and he opened the passenger door to let her in.

"You know what." Blair replied, still blushing.

"Au contraire," Chuck smirked, "I never pictured you to be the kind of lady to use such foul words as f-"

"Luck!" She interjected quickly, and sent him a proud grin that had him chuckling as he rounded the car and got in the driver's seat.

"Then I guess this is your chucky day," he drawled, and sent her an approving look as he fastened his seatbelt and turned on the engine. Utterly amused when she nearly shuttered in reaction to his obvious, and appreciative, scrutiny.

He pulled out onto the road, and they travelled up the hill in silence. He assumed she lived in one of the newly built villas and since she didn't object when he did a final left turn, he came to the conclusion that he had been right.

"So what do you do for a living?" Blair inquired. She had a feeling the calming sound of the car's engine might lull her to sleep, unless she engaged in some kind of conversation with her dark, mysterious savior.

Chuck shot her a look, drumming his fingers against the steering wheel, stalling the inevitable for a little while longer. He could never be sure on what reaction he would get in case he told someone of his, slightly un-orthodox, career choice. She was a little too young, even though he estimated they were probably about the same age, and too beautiful to have even considered exploring the services provided within his field of work.

"Had I known that was all it took to shut you up, I would have asked that question minutes ago," Blair teased him as he pulled over and the car came to a stop near her building.

He shot her a look and unbuckled his seatbelt. "I provide single women with casual company to dates or parties." He answered, and got out of the car.

Blair's mind was reeling and she could do nothing but stare at him, wide-eyed and her mouth agape, while he walked around the car. "You're a gigolo?" She shrieked, as he pulled her door open. She quickly made a move to get out of the car, only to let out a huff when she found herself being pulled back roughly into her seat by her still fastened seatbelt.

"No," he smirked, as he leaned in to unbuckle the seatbelt for her. He was suddenly very close, her nose mere inches from the neckline of his shirt and the paisley ascot there. Once again his cologne invaded her senses and caught her attention.

"I prefer 'professional dater'," he smirked, locking eyes with her. She suddenly felt light-headed and realized that maybe she shouldn't have had that last martini. Then he pulled away and extended his hand to her.

"You're an escort." Blair informed him, breathing a sigh of relief now that he was keeping his distance. "You get paid to…entertain women." She shook her head to rid herself of the image that should be less appealing that it was. That last martini had definitely been a bad idea.

"I'm not a prostitute," Chuck scoffed, as he accompanied her up the stairs of her house, "That's illegal you know. I just happen to be the perfect date." He added with a smug look on his face. Blair cocked an eyebrow doubtingly in his direction and he winked. "I could give you my list of recommendations, and my business card, to prove it."

She stopped and shot him a displeased look. "Do I look like I need to pay someone in order to go on a date?" She sneered, placing her hand on her hip and staring him down.

"Do I look like someone who gets paid for a date?" Chuck replied, and when she couldn't present him with a witty comeback, he let out another one of those addictive laughs. "I should get going. You can consider this a free sample of my services, Ms.-" He paused and looked at her, amusement glittering in his eyes.

"Waldorf," she found herself replying, even though she could hardly believe she was introducing herself to a gigolo.

"Ms. Waldorf, it's been a pleasure," Chuck said, taking her hand in his warm, bigger one, and placed a kiss on the back of her hand. Amused by the puzzled frown that appeared on her face in reaction to his gesture. Then he turned around and walked down the steps without looking back. Well on the street he shoved his hands down the pockets of his charcoal slacks, and walked towards his car whistling a tune she couldn't quite identify.

Blair realized she had been staring, when he reached his car and turned around, raising his eyebrow in glee. That smug smirk still firmly in place. She jolted then, and wiped the back of her hand with her other one in an attempt to rid her skin of the tingling sensation his lips had left behind. To her surprise she found that she was holding on to a small, black piece of paper. Flipping it over, she could make out letters in a shiny shade of black on the back of the card. His name was on there, as well as a phone number.

A business card. She had just been bestowed with a gigolo's business card. This really had to be one of the strangest nights of her life. With that thought in mind, she unlocked her front door and headed for bed. She fell asleep almost immediately and dreamed of wedding cakes, trips to Thailand and brown eyes.


"She turned Chuck into a whaaat?!"

So, what do you think? You up for more of this?

Please review and let me know what you think, and if you want me to continue!

Thanks for reading!