Author's Note: Very loosely based off the film Win A Date With Tad Hamilton.

Win A Date With Dean Winchester

Chapter One

Pamela's steely looking eyes glowered at Dean from across the desk as she drummed her fingers against the keypad next to her. To say that she looked annoyed was an understatement. Dean tried to give her the charming and winning smile that was plastered on buses, trains and billboards but it was no good. She pursed her lips and at that point Dean was convinced she was going to physically hurt him.

"Of all the boneheaded moves you have pulled in your time this is probably one of the stupidest." Pamela snapped. "You really had to pick now to do something like this didn't you?" She then asked looking away from Dean to furiously type something on her large computer.


"Shush. I don't want you to say anything, do you hear me?" Pamela said without looking away from her screen. "I've been on the phone for three hours already and it's only ten in the morning so I really do not want to hear it Dean. I might be able to stop any publication of the offending photos but it is going to take a freaking miracle to manage. Honestly Dean, you really don't make things easy sometimes."

"Listen Pam-"

"I said 'shush' so shush." Pamela muttered. "I've only just got the phone to stop ring-" As if on cue the intercom on Pamela's phone buzzed.

"Miss Barnes, there is a reporter of The New York Post on the line wanting to speak to you." The voice of Pamela's assistant said filling the room. Dean couldn't help but give a mutual groan along with Pamela.

"Yes thank you." Pamela said closing her eyes and rubbing the ridge of her nose. She picked up the voice and tried to put on her cheeriest voice. "Yes this is Pamela Barnes" Dean then tried to drown out everything else that she was saying as he looked out the window at the New York skyline. Pamela was clearly pissed at him and he could understand that but he wasn't sure why she was this pissed at him. True maybe now wasn't the right time to have done what he had done considering he'd just been nominated for several 'Best Actor' awards at teen award shows and this probably wouldn't give him the best of reputations but did Pamela really have to glare at him that much?

"Pamela?" Dean asked and Pamela raised a finger for him to give her a minute. Dean leant back in his seat and went back to staring out the window. A loud sigh from Pamela drew Dean back from staring at the skyline.

"I hate the press sometimes." Pamela muttered under her breath as she hung up her phone. "Right I think I can sort this whole mess out but it is going to take some magic to make this all go away. In the meantime can you promise me that you're not going to do anything else that will end up with your face splashed across the tabloids?"

"I can't promise you anything Pam." Dean said grinning. Pamela's frown deepened and dean realised that this was not the time to try and joke with his agent. "Ok, ok fine. I'll try. Am I excused?"

"Yes, yes you can leave now." Pamela said shaking her head as Dean rose from his seat. "Oh and Dean? The next time you decide to get a blowjob from some skinny homo in Greenwich Village either decide against it or look to see if there are any bloody photographers around that will certainly end up photographing said blowjob and selling it to every single paper in America! Now go before I decide to make your next role one in a very cheesy and sickening chick flick" Pamela snapped pointing at the door that Dean swiftly raced out of.

Well that whole thing could have gone better.

"God, I cannot believe you sometimes" Jo said laughing loudly as Dean sipped his coffee. The two of them were sat outside a café near Dean's apartment and Dean had just been going over his meeting with Pamela that morning. "You Dean Winchester are ridiculous. What were you even doing in Greenwich in the first place?" Jo asked stubbing out her cigarette in the nearest ashtray and picking up her own cup of coffee.

"I was at this party." Dean explained.

"That doesn't cover half of what I'm asking here, so spill it Winchester." Jo said rolling her eyes heavily at Dean. Dean knew exactly what Jo was asking but that would take a lot more explaining than Dean wanted to do at the moment. "Come on Dean."

"I was drunk, it was a crazy party and that was that." Dean said sipping his coffee again.

"That also doesn't cover half of what I'm asking." Jo said. "I wonder why we're even friends sometimes." Jo muttered rolling her eyes.

"Because I stuck up for you all the way back in first grade when some asshole thought it was funny to push you over in the playground." Dean said.

"I punched that dickwad in the face straight after he pushed me over." Jo pointed out.

"I helped though." Dean said smirking. Jo rolled her eyes again but smirked back. "I'm a brilliant friend and you know. You wouldn't have met Al Pacino if it wasn't for me." Dean pointed out.

"That is true Winchester." Jo said. "Now you could be an even better friend by going and getting me another coffee." Jo added handing Dean her mug. Dean sighed put took Jo's mug from her and walked back into the café. For a Wednesday afternoon the place was pretty quiet and Dean appreciated that because it meant there would less of a chance for someone to recognise him and ask for an autograph. Dean didn't mind talking to his fans, in fact he really loved it sometimes but he really wasn't in the mood right now thanks to his meeting with Pamela that morning.

"Hey there, can I get two more coffees please?" Dean asked the girl behind the counter. She nodded dumbly and set about filling the mug Dean brought in with coffee. "Thanks" Dean said giving the girl a wink before handing over a couple of dollars. He waltzed back to where Jo was sitting and quickly sat back down.

"I'm still amazed you haven't given Pamela a heart attack with some of the shit you have pulled in your time. Do you remember when you were drunk on The Late Show?" Jo said reaching for her coffee and taking a liberal gulp.

"No…that could have been because I was drunk though." Dean said with a chuckle. "Still Pamela thinks she can work her magic and sort this whole thing out."

"She's going to have to be a freaking wizard to sort this out. Still, if you could explain what happened then that might help." Jo said.

"I told you Jo. I was at a party in Greenwich and got too drunk. That's all."

"Yeah sure thing Winchester. Sure thing." Jo said sounding like she didn't believe Dean one tiny bit. "I'm just going to wait to hear what Pamela has in store when it comes to damage control. Remember when you accidentally swore at that awards show and Pamela made you do that cheesy made for TV movie about the dying woman desperately seeking love?"

"Don't remind me. Sam still likes to send me YouTube links to the crappy final scene at least twice a month." Dean said shuddering at the thought of that terrible film.

It took Castiel several minutes of rummaging in his backpack to find his keys and by the time he got through the front door he wished that he had stayed in the library once he saw his twin sister Anna sat on the couch with a huge bowl of popcorn and a stack of DVDs. Oh crap Castiel thought as he placed his bag on the floor. How could he have forgotten Anna's Wednesday night tradition? Every Wednesday night Anna would set up camp on the couch with popcorn and whatever crappy Dean Winchester film she felt like watching even though she'd seen them all too many times for Castiel's liking.

"Oh hey there, did you get everything at the library done?" Anna asked smiling up at her brother.

"Yes, I think so. Which mind numbingly terrible film are you burning your retinas with tonight?" Castiel said walking towards the kitchenette adjacent to their small lounge.

"Very funny Castiel." Anna said. "We can't all love terribly depressing French noir films."

"There is nothing wrong with French films." Castiel said shrugging.

"There's nothing wrong with Dean Winchester films." Anna shot back.

"There is plenty wrong with his films Anna." Castiel said as he looked into the fridge for something edible. There was not a lot of choice. Castiel sighed and went to grab the Chinese take-out menu attached to the front of the fridge. "Do you fancy a take-out?" he called out to Anna.

"You're a film snob Castiel." Anna said throwing popcorn into her mouth. "Nah, I've eaten too much take-out in the past two weeks. One of us needs to learn how to cook and by that I mean you can learn how to cook."

"Yes because we both know that is not going to happen. I hate to bring up the chocolate muffin incident of 2008 but I will have to." Castiel said.

"Point made and taken. I think Gabriel is still too traumatised to even look at a muffin." Anna snickered. "Now come and sit down, the film is about to start."

"It's not the one where he plays a depressed solider tore between his love for his country and the local village girl is it? Because that film was the worst film I have ever been forced by you to watch. That was two and a half depressing hours of my life I will never get back thanks to both you and Dean Winchester."

"I love that film! It was Oscar nominated!" Anna said sounding aghast.

"It was a terrible film Anna and I won't believe otherwise." Castiel said looking through the Chinese take-out and trying to decide what to order. "Are you sure you don't want any take-out?" he asked Anna.

"I'm sure, thanks anyway." Anna said. "You sure you don't want to sit and watch the film with me?" Anna then asked patting the space next to her on the couch.

"I'm quite sure Anna, there's only so much of Dean Winchester's bloody face I can take in one night."

"He's gorgeous and you bloody well know it Castiel!" Anna said with a chuckle. Castiel rolled his eyes and went off to order his food which he would no doubt be eating in his room to get away from his sister's adoration for Dean bloody Winchester. So while Anna sat on the couch eating too much popcorn Castiel stayed in his room eating chicken and broccoli noodles while working his way through one of the many books in his room.

On Friday morning Dean was called into Pamela's office and he knew this meeting would go one of two ways. One way would probably end up with Pamela brutally killing Dean and his blood covering her pristine office. When he got to Pamela's office, late because of the obscene amount of traffic, Pamela was sat behind her desk and tapping her foot loudly against the floor.

"Sorry I'm late Pam, the traffic was a bitch." Dean said giving Pamela and cheeky smile. Pamela rolled her eyes but didn't shout at him so Dean guessed he was forgiven. "What's this about?" Dean asked as he sat down opposite Pamela.

"I've managed to carve out a deal with the press. They won't release the photos as long as you do something good for charity and something that will smell lots of papers. I'm not going to be remotely modest about this, it was a freaking good idea and I am a God for sorting all this out." Pamela said actually smiling. Dean couldn't help but look at Pamela with confusion because he honestly couldn't see where this was going.

"So the plan is?"

"The brilliant plan Dean is that we set up a competition to win a date with you and for every entry there will be a dollar donated to some charity. It will give good publicity and hopefully the press will be sweet talked enough into not publishing those damn photos" Pamela explained.

"Wait…someone will win a date…with me?" Dean asked.

"Yes. The lucky winner will have a delightful evening out with you at some very nice restaurant and you will not act like a dickhead at all." Pamela said sounding stern in a way that meant there was no possible way that Dean could act like a dickhead.

"Why would anyone want to win a date with me?" Dean asked because if he was being perfectly honest he couldn't understand why anyone would. Sure he was a famous actor but he was sarcastic and quite blunt, they weren't normally qualities people looked for in potential dates.

"Don't be stupid Dean, you weren't voted 'Hottest Actor' by all those damn magazines for your personality." Pamela said rolling her eyes. "Now do I have your agreement to this whole thing? Because to be honest I've already gone ahead and started arranging it."

"Thanks Pamela, thanks a whole lot." Dean said with frustration. "You can't fix the winner can you? I don't want to end up with some back-water hillbilly"

"No, I cannot fix the winner Dean; you will just have to suck it up and try to be charming for one night." Pamela said. "If you screw this up I will kill you Dean and I mean it." Pamela added warningly. For that moment Dean was actually scared that his agent would kill him and she was skilled enough to make it seem like a complete accident.

Castiel was coming out of his last class of the day when the phone in his pocket buzzed several times in just a minute. Sighing to himself he pulled the phone out of his pocket and looked at the screen. Four texts from Anna and all of them had been sent barely seconds after one another. Either she was dying or something monumental had happened to her. Maybe she had finally managed to open that one cupboard in their apartment that they had never been able to open. In Castiel's eyes that was quite monumental. Castiel reached the nearest bench, sat down and read Anna's texts.

Anna Milton:



God I wish I was lucky

Do we have any jelly beans in the cupboard?

Castiel really did not know what on earth Anna was on about and part of him really did not want to either because an excited Anna was almost as dangerous as an excited Gabriel which was in connotation with the apocalypse.

Author's Note: I blame my sister for this because she made me watch 'Win a Date With Tad Hamilton' this afternoon and I was reading a Destiel fic at the time. Then bam, brain crack hit me and I had to start writing this even if it is terrible. If people don't hate this idea then I will carry on writing so reviews will be helpful.