A/N: A re-imagining of the 1990 film with a sprinkling of SPN cast members. Since it's an AU, some details may be slightly different. I hope you enjoy!

DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Castiel Novak moved through the crowd of people with his usual serious, focused expression. He smiled thinly but politely at the people who spoke to him but he did not go out of his way to make conversation. The entire event had been put together by his lawyer, Fergus Crowley. Castiel hated the 'mixers' but recognized the necessity of them for business contacts. Now, as he listened to a very irritated female voice on his phone, he was even more reminded why interacting with people was something he truly did not enjoy.

"Meg ... Meg, I told my assistant to make the arrangements ... did she not call you?" Castiel said, pinching the bridge of his nose.

"Of course she called me, Castiel ... I talk to her more than I do you." The sultry voice he'd once adored sounded tired and plain now.

Castiel sighed. "I see." He knew where the conversation was headed and he wasn't sure what bothered him more – the end of yet another relationship or the fact that it didn't hurt as much as he thought it should.

"I have my own life, you know, Castiel," Meg snapped.

"This is a very important week for me, Meg. I – I need you here." Castiel said, trying one last time to extend his apology.

"But you never ... and I mean never ... give me any notice, Castiel!" Meg's voice turned cold. "You just think I'm at your beck and call."

Castiel sighed. "I do not think you are at my beck and call, Meg ... "

"That's the way you make me feel every time you pull this shit, Castiel. I'm seriously considering moving out."

"If that's what you want to do, Meg," Castiel replied tiredly.

"Fine – when you get back to New York, we'll discuss it," Meg said reasonably.

Castiel felt a flare of irritation. Meg was good at back-pedaling ... she'd throw him an ultimatum and then back away before anything permanent could occur. "Now is as good a time to discuss this as any, Meg."

There was a moment of silence on the line. Castiel imagined she had realized that she was on the verge of ending what, for her, had been a rather advantageous relationship. He assumed she would now begin to apologize or soften the blows she had landed. Instead, Meg surprised him.

"Fine. Good-bye, Castiel."

The line disconnected. Castiel blinked and regarded his mobile as though it had personally offended him. "Good-bye, Meg."

He tucked his phone back into his suit and sighed. Yet another failed effort to find someone ... anyone to share his life with. Castiel was beginning to think that perhaps he wasn't meant to have that special person to come home to ... to share his interests and his dreams. Castiel shook his head wearily. Did he still have dreams?

"Fergus suggested that I - "

Castiel glanced at the young man walking beside him – a young up and coming executive in his company, no doubt. "Crowley is just my lawyer. He does not make decisions for this company."

The young man swallowed hard. "Yes sir."

"Now then, what did the Singer stock open at on the Nikkei?" Castiel asked.

The young man looked at him blankly. "I don't know, Mr. Novak."

Castiel sighed. "You don't know?" He glanced at his watch. "Tokyo opened approximately 90 minutes ago. You need to keep on top of this."

"Yes sir."

Castiel gave a genuine smile to the young man and was pleased to see him relax. He remembered all too well the lessons he had learned on his own climbing upward. "It's alright but I want this wrapped up as soon as possible – I need to be back in New York by Sunday. I have tickets to the Met."

With that, Castiel turned and waded back into the milling crowd of people. He found the coat room and collected his long coat. He turned when he heard his name called. A lovely young redhead approached him with a broad smile. Castiel returned it.

"Anna!" Castiel had dated Anna Milton some time ago and he still remembered the relationship and Anna with great fondness. He pressed a kiss to her cheek.

"I was so sorry to hear about Michael," Anna offered softly.

Castiel flushed but he nodded. "Thank you. I heard you were now married."

Anna smiled the bashful smile of a woman in love. "Yes ... I couldn't wait for you, Castiel."

Castiel chuckled. A thought ocurred to him and he turned to Anna. "Anna ... when we were ... dating ... did you talk to my assistant more than me?"

Anna laughed, a gentle sound that Castiel had always enjoyed. "She was one of a my bridesmaids."

Castiel sighed and gave her Anna a sad look. Then he shook off his melancholy and gave her another kiss on the cheek. "Your husband is a very lucky man, Anna. Best of luck to you both."

Crowley smiled at the lovely young woman sitting across from him. He wondered exactly how much complimentary conversation he was going to have to make before she would sleep with him. Opening his mouth to comment on her eyes, Crowley felt a cold hand land on his shoulder. His wife's long manicured nails dug into the muscle. He looked up, annoyed.

"Lilith, what -"

"He's leaving ... Castiel is leaving," Lilith said in a voice just a shade below a panic.

Standing, Crowley excused himself and walked quickly out to the drive where he'd seen Castiel disappear. His heart – what little of it there was – fell into his shoes when he saw Castiel standing next to his lovely new Lotus Esprit.

"Oh no ... um ... Castiel? Uh ... what seems to be the problem? What's wrong with the limo?" Crowley chattered nervously.

Castiel gestured vaguely toward the back of the drive. "The limo is unavailable ... Garth cannot get it out."

The driver, Garth, smiled broadly and shrugged as if to say, Whatcha gonna do?

"Do you have your keys?" Castiel asked.

"Uh .. yeah, here ... wait, darling, let me see if I can work something out, Castiel ... you probably shouldn't be driving ..." Crowley said frantically.

Castiel ignored him and got into the car. He glanced over the dash and sighed. It would have to do.

"Castiel, are you even familiar with a stick shift?"

"Of course I am, Fergus." Castiel replied absently. He wasn't but he had not made his way in the world by revealing his weaknesses.

Crowley groaned. "Oh alright ... but please, dear, be ginger with it ... it's rather new ... oh please, Castiel!"

Castiel braked to a stop at the end of the drive after grinding the gears into place. "Do not worry, Fergus ... I love this car."

"No you don't ... Castiel you'll get lost in the dark ... Beverly Hills is down the hill!" Crowley shouted as Castiel turned and drove off going the wrong way. Crowley cast a pleading look toward the sky as if to ask Why me?

Reaching over tiredly, Dean Winchester shut off the ringing alarm. He stretched and yawned before flopping back against the pillow. Another night ... another couple of hundred bucks – if he was lucky.

With another yawn, Dean rolled out of bed and walked sleepily into the bathroom. He slept nude so he just took care of mother nature then stepped into the shower and began the nightly ritual of preparing for his evening job. Shampoo – lather, rinse, repeat. Shave – make absolutely sure he didn't have any stubble, smooth off the chest and trim a little down below. Use a non-scented soap that wouldn't clash with his cologne. Check nails – trim and clean. Dean could have slept through the entire process, he was so used to it by now. Stepping out, he brushed his teeth and checked his hair – he kept it short cropped although he did have a regular that preferred it longer. He had a wig for those nights.

Going back into the room, Dean slid on a pair of black boxer briefs and checked himself in the mirror. They showed off the package nicely without being too overt. Pulling on a pair of soft, worn jeans that hugged his ass, Dean again eyed the result. He debated for a bit over the shirt and finally decided on a fitted green button down – it brought out the color in his hazel eyes. Tucking it in and putting on a belt, Dean unbuttoned the shirt almost halfway down his torso. He put the non-scented lotion on to help enhance the smooth appearance and then pulled on his work boots. For whatever reason, the johns he attracted really liked that sexy blue-collar look. Dean didn't care as long as they paid and he could get the job done with a minimum of fuss and muss.

After making sure he had his i.d. and key tucked in the sole of his boot, Dean went back into the bathroom and pulled a couple of items from the medicine cabinet. Leaning in close, Dean put just a small line of light brown eyeliner on and applied the clear mascara carefully. He'd learned early that clear or not, the shit burned like a mother if he got it in his eye. After he was satisfied with the way it made his already thick lashes stand out, he put clear lip gloss over his bottom lip and pressed his lips together. The effect, when he held his mouth open just slightly, gave him the 'pretty boy' look that Gabe called his money-making gift. Dean studied his face in the mirror one last time. When he was getting ready for work, Dean never made eye contact with himself in the mirror. It was easier not to have to justify what he was doing that way.

Tucking the lip gloss in his pocket for reapplication later, Dean grabbed his black leather jacket and headed out the door. He was halfway down the staircase when he heard the landlord berating another tenant about paying rent. Dean groaned. He'd forgotten it was already the end of the month. Running back to the apartment as quietly as he could, Dean went into the bathroom and lifted the lid from the back of the toilet. He pulled out a plastic soap case to get the money he and Gabe put aside for rent each month. His stomach flipped when all he saw was a dollar bill.

"Fuckin' Gabe..." Dean growled.

Unable to go out the front door, Dean went to the window beside his bed and slipped out onto the fire escape. He lowered the ladder and climbed down to the junk-strewn 'courtyard. Someone had cut a neat hole in the chainlink fence that surrounded the area and Dean simply ducked through it and went in search of his roommate, Gabriel.

Walking down the crowded sidewalk, Dean ignored pretty much everyone until he passed by an alleyway. Cops and EMTs milled around the entrance and he could see a body lying just beside a dumpster. Dean glanced over at the detective talking to a beat cop and snuck around to get a better look. When he saw who the body was, his already twisting stomach wound even tighter. He turned away, pale, and walked on quickly.

Dean went into the club he and Gabe frequented when they weren't working – which wasn't often. It was a place to hang out and the proprietor, Benny, was a reasonably nice guy. He also thought Dean was 'damn cute', which got him a free beer from time to time. Leaning over the bar, Dean shouted to be heard over the music.

"Yo, Benny! You seen Gabe?"

Benny looked up from washing a glass and inclined his chin toward the stairs. "In the pool room, darlin'."

Dean grinned his thanks. Benny was from Louisiana and his accent was thick and soft, which Dean thought was very alluring. He'd had a casual thought about hooking up with the bartender but he didn't want to screw up a good thing which is what they had now. No expectations, just casual friendly acquaintances – it was easier that way.

Dean went up the stairs and was not happy to see Gabe leaning back in his chair with his eyes closed and a happy little smile on his face. The older man sitting close with his arm around Gabriel looked up and gave Dean a sly look intended to be seductive. It just made Dean's already churning stomach threaten to erupt. Ignoring the man, Dean looked down at his drifting roommate.

"Is it all gone?" Dean said loudly.

Gabriel opened bleary eyes and looked at Dean. "Dean-o! Alastair, you remember my roommate, Dean ... that's Ruby and - "

"I know everyone! Is it all gone, Gabe?!" Dean asked angrily.

"Alastair sold me this great shit ... we had a party ... " Gabriel giggled. "I got to be the hostess!"

"I can't believe you bought dope with our rent ... what the hell is going on with you, Gabe!" Dean snarled, walking over and grabbing Gabriel by the arm and pulling him out of his chair.

"I needed a little pick-me-up, Dean!" Gabriel said, pulling away.

Dean let go and Gabriel struggled to keep his balance. "Yeah? Well we need rent money!"

"Easy, now, Dean ..." Alastair moved to put himself between Dean and Gabriel. "Gabe only owes me 200 more ..."

Dean blinked and stared at Gabriel who was blushing and not meeting Dean's eyes. "Another 200 dollars?"

Gabriel gestured broadly. "That was from way before, Dean."

Alastair gave Dean the look again. He seemed to be appraising Dean's body. "That's right, Dean – 200. But if you want to work off his debt with me ... I'm sure something can be arranged."

Gabriel rolled his eyes. "Sweet offer, Alastair, but not now. Come on, Dean ... downstairs." Taking his roommate by the arm, Gabriel dragged Dean back down to the bar.

"What would we work out, Gabe, huh? What?" Dean demanded. "And what the hell with the money, Gabe? You took it while I was sleeping?"

"You were unavailable for consultation," Gabe replied.

"Fine ... come on ..." Dean said heading to the door.

"Snack!" Gabriel yelled.

Dean rolled his eyes and followed Gabriel to the end of the bar where he began to load up a cocktail napkin with fruit garnishes. Dean sat beside him glumly.

"Besides ... it's my apartment," Gabe grumbled.

"Yeah? Well I have to live there too, Gabe!"

"Look, you came here, I gave you some money, I gave you a place to stay and some valuable vocational advice. Alastair was on my case, I had to give him somethin' so don't irritate me, Dean."

Benny glanced down the bar and growled. "This ain't a buffet, Gabe."

Gabe rolled his eyes and sat back with a napkin loaded with cherries and orange slices.

"Irritate you?" Dean said incredulously. "I just saw ... I just saw Adam being pulled out of a dumpster!"

Gabe nodded sadly. "Yeah, I know. He was back on meth ... Uriel was trying to clean him up for months."

Both of them turned when a fight erupted in the back of the bar. They turned away when it didn't immediately affect them and Dean sighed. "Don't you wanna get out of here, Gabe?"

"Get outta where? Where the fuck you wanna go?"

Dean looked down at the bartop and shook his head. He had no idea.