Okay, so here's my new fan fic! I was watching Win A Date With Tad Hamilton, and thought it'd be cute to make the story for Chuck & Blair! Very AU and OOC, but still lots of CB goodness!! I hope you guys like it, let me know if I should continue!

Disclaimer: I do not own Gossip Girl or Win A Date With Tad Hamilton.

Win a Date with Nate Archibald

Summary: Chuck, Blair and Serena are best friends living in Brooklyn, New York. Their lives suddenly change when Blair wins a date with Nate Archibald, the most famous actor of their time! Based on the movie Win a Date with Tad Hamilton! AU & OOC. Chuck & Blair, of course.

Chapter One

"Hello Betty," he said in a brooding tone looking at the girl who had broken his heart. "Shouldn't you be at the hospital with a certain other soldier?"he asked.

"Is there any way you can find it in your heart to forgive me?" Betty pleaded with sad eyes.

"I wonder if these two get together," Chuck Bass whispered sarcastically to his two best friends, Blair Waldorf and Serena Van der Woodsen, as they watched the final scenes of the movie play out on screen.

"Shhhh!" Blair and Serena both hissed back at him trying not to miss a moment of the movie. Chuck rolled his eyes as he couldn't believe how pathetic this movie was. And what was even more pathetic is that his friends were actually buying into it.

"I'll forgive you on one condition," he said.

"What's that?" Betty asked, hope in her eyes.

"Dance with me," he demanded as he reached his hand out for hers. She quickly grabbed his arm and jumped into his arms for a romantic kiss. The danced in the moonlight to the music playing from the car stereo looking as happy as ever.

Blair and Serena both sighed at the unbelievably romantic moment. Chuck just rolled his eyes again, shocked that such a cheesy line made all of these women in the theater swoon. Blair and Serena applauded loudly as the credits began to roll.

"Explain one thing to me. What kind of desperate and pathetic emotional cripple…would actually buy that as an ending?" Chuck asked, still confused as to how such a stupid ending was considered good. He looked over and saw that both Blair and Serena had tears in their eyes and he just rolled his own again. Of course," he thought, not really surprised that the movie had affected his friends that way.

"Blair, do you think that in real life Nate Archibald is the man that he seems to be on the screen?" Serena asked, completely ignoring Chuck's comment. She was still swooning over the amazing performance that they had just witnessed.

"Oh, absolutely!" Blair responded. "I mean, you can't just fake that kind of thing," she continued.

Serena nodded and took Blair's hand. "What do you think Nate Archibald is doing right now?" she asked.

"I'll bet he's in church," Blair responded squeezing her best friend's hand.

Chuck rolled his eyes again, what is that four times tonight? How foolish could these two girls be? If he were Nate Archibald, the most famous and highest paid movie star of the year, he most certainly would not be in church right now. "You guys are seriously delusional," Chuck said as he began to stand up to exit the theater.

The two girls just rolled their eyes and sighed as they followed their friend out of the theater. When they got outside, Blair realized that it had gotten a little chilly. Chuck immediately noticed her shivering, so he took of his jacket and put it on her shoulders.

"Thanks," Blair said smiling. They walked down the streets of Brooklyn on their usual path after seeing a movie. Serena's apartment building was the first one they hit.

"Okay guys, goodnight! See you at work," Serena said as she made her way up the stairs to let herself into the building.

"Goodnight, S" Blair called after her. Blair and Chuck waited until she got safely into the building before continuing their way home.

****

"That movie was so amazing. I think that was Nate's best performance yet," Blair said, making conversation as they walked hearing the sounds of the city surrounding them.

Chuck rolled his eyes. "Are you kidding me? That movie was as pathetic as all the other movies he's in," he said with a disgusted tone.

"Whatever, Chuck. Just because you don't have a romantic bone in your body doesn't mean you can't enjoy a good chick flick every once and a while," Blair commented.

"Actually, that's exactly what that means," Chuck replied with a smirk on his face.

"Look, you can put that smirk on all you want. I know that somewhere deep down inside you there's a hopeless romantic just waiting to come out," Blair said teasingly. She knew it was true though.

"And what is it waiting for, I wonder," he said playing along.

"I don't know exactly. I think that it's waiting for the right person. Somewhere out there is the girl of your dreams Chuck Bass, and when you meet her, that romantic will want to come out," Blair said.

Chuck didn't say anything. He just looked at his best friend incredulously. God, she's beautiful, he thought. If only she knew that maybe she was that girl. But, it was pointless, Blair Waldorf would never settle for Chuck Bass. She deserved much better than that, and Chuck knew it. He immediately shook away his thoughts and responded. "Please, you forget who you're talking to." He was Chuck Bass after all. And Chuck Bass did not have girlfriends. Nor was he romantic. Although, he couldn't help but think that if he did have a girlfriend, and if he was to be romantic with anyone, it would be Blair Waldorf. But he could never tell her that.

"So do you," she shot back. "You forget that I've known you since we were five. That's eighteen years of knowing someone. I know everything there is to know about you, and I know what you could be capable of." Blair knew that if Chuck just let go of all the ridiculous womanizing ways he had gotten himself into after high school, he could make some girl really lucky someday.

You don't know everything about me, he thought. If you did, you'd know that I've been in love with you since we were five. "Whatever you say, Waldorf," he said throwing her another smirk.

"I know I'm right," she said pointedly. "You just wait Chuck Bass."

****

They continued their walk silently to Blair's house and found her father sitting out on the front porch reading the paper as he always did at night. "There you guys are! How was the movie?"

"Hi daddy," Blair said as she gave him a hug. "It was amazing, of course. Nate Archibald is amazing."

"Always swooning over that Archibald, aren't you sweetie," her father said laughing. "What about you Charles? Did you enjoy the movie?"

"I can't say I liked it as much as Blair here did, Harold," Chuck laughed.

"Well, I figured. You really are a great friend, Charles, always accompanying Blair and Serena to those movies even when they are complete torture for you," Harold said laying a hand on Chuck's shoulder.

"Only for them," Chuck said winking at Blair. She smiled in return. "Well I should get back to the apartment, call it a night."

"Yes, of course. You all have work in the morning don't you?" Harold asked.

"Bright and early, sir," Chuck said getting up from the couch on the porch. "Good night, Harold. Good night, Blair."

"'night Chuck," Blair said as she leaned onto her dad's shoulder.

"Good night, Charles," Harold called after.

When Chuck was out of sight, Harold turned to his daughter. "You really are lucky, you know, to have a friend like Charles."

Blair smiled up at her dad. "Yeah, I am. He's always been there for me."

"You know, you two would make an excellent couple," her father said teasingly. He knew the way Charles looked at his daughter. He liked the boy; he would be good for Blair.

"Dad, it's not like that at all. I've known him forever, he's just a friend," Blair responded almost laughing.

"Alright, alright, I'm just saying."

"Oh, you're just saying, huh?" Blair laughed. "Okay, I'm going to bed. Good night, daddy." She gave him a kiss on the cheek, stood up from the couch and headed inside.

"Good night, sweetheart," he called after her.

****

As Blair got ready for bed, she couldn't help but think about what her dad had said. Her and Chuck a couple? Sure, he had devilish good looks and a charming personality. But he was her best friend, it'd be weird. Besides, he liked to play the field, and Blair was a one man kind of girl. As she turned the light off in her room and got under the covers of her bed, her thoughts immediately went away from Chuck and moved to Nate Archibald. Boy was he dreamy, she thought as she drifted off to sleep.

What do you guys think? Should I continue? Review please!