Hello everyone. I'm a huge fan of crack and cross-over ships and Gossip Girl and Glee are two of my favorite shows so here we have it. Chuck/Rachel or as I like to call them: Chuckleberry. Enjoy!

He watches her as he had been doing every night for two weeks. Dark eyes focused on her tiny body as she stands in a pair of high heels that she struggles to stand up in, possibly due to her current state of intoxication. She stands on the make shift stage at the front of the bar, belting out the last notes of a sad love song he can't quite place. She's beautiful, he thinks. Her round chocolate doe eyes and wavy brown hair reminding him more of another petite brunette more than he'd care to admit.

She hops off the stage gracefully, or as gracefully as she could being more than a little dunk and in ridiculously high heels. Her audience- a room full of drunken old perverts wanting to escape their wives and children- applauded her, some offering wolf whistles and leers as she walks by, making a bee line towards the bar.

She struts over, the heels of her stilettos clicking against the wooden floorboards. She comes and stands next to him as she beckons the bartender over. His breath catches in his throat. She was breathtaking, even more so up close than on the stage. She flashes the barman a bright, but entirely insincere smile and orders a scotch. He raises an eyebrow. She seemed more of a martini type of girl.

"Make that two," he tells the bartender, identified as Tyler by the badge on his black polo shirt.

The brunette singer stares at him in mild surprise. "On me." He assures her with a one-sided smirk.

She nods, accepting her drink and taking a long sip. "Rough day?" The dark haired man asks, raising his own glass to his lips.

"The worst," she murmurs into her glass. Her eyes are downcast but still beautiful. Bright chocolate orbs framed by thick, dark lashes. Just like-...No. No, she was gone now. Off into the sunset with Prince Charming. She wasn't his anymore. They were over- for good this time, no more second and third and fourth chances. His heart still constricted at the thought. He turned his attention back to the nameless beauty with the sad eyes.

"Want to talk about it?" He asked.

"Not particularly." She replied, wondering why this stranger cared about her problems. Probably a way to get her to sleep with him. She almost smirked at the thought. Good luck with that, Mr. Armani Suit, she wasn't into that type of people.

"I'm Chuck Bass." He informed her, briefly remembering when the mere mention of his name had women begging him to take them home.

"Rachel."

"No last name?"

"Nope."

"Alright then. Any reason why a pretty girl like you is in a place like this?"

"You won't give up will you?" Rachel asked with a dramatic eye roll, though her tone was more amused.

"No, I'm very persistent. I always get what I want." He smirked, although he knew that was a lie. The only thing he had ever wanted didn't want him back and that killed him.

"Alright Mr. Bass, since this is New York and the chances of us bumping into each other again are extremely slim I'll tell you," she decided. Chuck neglected to tell her he had been watching her sing for the past two weeks in this bar. She didn't need to know that. "But only if you tell me why you're here at a place like this, when judging by your suit you have more important places to be."

He gestured for the bartender to bring them over more drinks. If they were going to be exchanging life stories he'd need to be at least halfway to being drunk.

"My husband left me," Rachel blurted out after a short silence. Chuck's head snapped up. Husband? She looked so young. 19, 20 at the most. "He said he couldn't be with me while I was still hung up on my 'stupid Broadway pipe dream' and I was selfish for wanting him to leave Ohio with me while he had his step-dad's garage to run."

Chuck snorted, "Your husband is an idiot. Anyone who leaves someone like you to run a two-bit garage in the South of Nowhere doesn't deserve either you or New York."

Rachel smiled at him, a light blush gracing her cheeks. "Thanks, so what about you, Mr. Bass? What's your story? Why are you in a damp and dingy bar in the Lower East Side at this time of the night?"

Chuck thought about spinning her a fake story but she was bound to find out eventually. It was all over Gossip Girl anyway.

"The only girl I've ever loved got married to a prince. Every time I go home I am constantly reminded that she is not and will never be mine. Everywhere in the Upper East Side makes me think of her and all the places we have ever been together. I am plagued with thoughts of how we could have been together if I had only done something sooner. Besides, my step-mother has told all the bars in the Upper East Side not to serve me."

Rachel reached out and took his hand in her own soft, small one. "I'm so sorry Chuck. If it makes you feel any better this girl sounds like she made the wrong decision by marrying that prince. Anyone who loves someone else that much deserves happiness."

"I appreciate the thought Rachel, but Blair is the one who deserves happiness, she deserves any and everything that Prince Louis will give her."

Rachel flashed him a grin, then looked at her watch. "Oh, gosh. I've got to be getting home now Chuck. I'll see you around. And thanks for the drinks."

He watched her walk for about fifteen seconds before he called her name. "Rachel! Wait a second." The brunette turned around, waiting for her companion to catch her up.

Chuck smiled. "What kind of a gentleman would I be if I didn't escort you home?"

"You don't have to..." Rachel protested weakly.

"I know. I want to."

Rachel's apartment building was nice. Homely. It was in the center of Manhattan, near Central Park. On the walk there Rachel informed him that her dads (yes, plural) had found and paid for it because they didn't want her living on college campus. He also learned that she was in fact 19 but had taken a year off before going to college to marry her High School boyfriend Finn Hudson, who he had been told, had once been Quarterback of McKinley's (her alma mater) football team. He also found that Rachel liked to talk. A lot. Mostly about herself. She had dreams and ambitions that were bigger than she was dreams that her moronic husband were standing in the way of.

He walked her up several flights of stairs because the elevator was broken. He wasn't used to taking girls home. Usually he'd pick up a random slut and take them to his hotel suite at The Empire. He was growing up.

When they reached her door they lapsed into a comfortable silence, neither knowing what to say.

"So..." Rachel trailed off.

"When can I see you again?" They both blurted at the same time.

Rachel giggled nervously. "Do you maybe want to, um, go out some time?"

Chuck smiled at her. Maybe this was what they both needed. He an escape from the memories of his past and her a new beginning away from both her husband and Ohio. "I'd like that Rachel. I enjoy spending time with you."

The brunette beamed at him and pulled a business card from her purse.

Rachel B. Berry

Actress/Singer/Future Star, was written on it as well as her cell and home numbers.

Berry, he mused. Definitely suited her more than Hudson.

"Call me- anytime." Rachel told him. "Good night Chuck."

"Good night Rachel. I'll be seeing you very soon."

"Why does that sound like more of a threat than a promise?"

"Because it is. Like I said, I'll see you soon." He leaned down and gave her a swift kiss on the cheek before turning on his heel and leaving a very surprised and breathless singer at her door.

Chuck Bass walked into a dimly lit bar in Central Manhattan, it was one he had been frequenting for the past two years. He took his usual seat next to the bar, a glass of scotch was immediately placed in front of him. He sipped it slowly as a small brunette with bright eyes and a brighter smile stepped onto the makeshift stage in the center of the room.

"Hi everyone, my name is Rachel Bass and I would like to dedicate this song to my husband..."

You've been on my mind
I grow fonder every day,
Lose myself in time
Just thinking of your face
God only knows
Why it's taken me so long
To let my doubts go
You're the only one that I want

AN: I'm back! Hello lovelies, a few months ago I put up a poll asking if people wanted a Chuck/Rachel story and I got a positive response so here it is. It was extremely delayed due to unforeseen circumstances (people who have been reading Samchel Snapshots will probably know what I'm talking about, and on that note I have an update planned for that as well) but I am back now so expect to be seeing and reading a lot more from me. I would like to thank everyone who has been wishing me well, your thoughts are much appreciated. Oh and the song is 'One and Only' by the wonderful Adele. Reviews would be lovely.