A/N: So this is my first finished GG fanfic! The show has been frustrating me so I had to get this out. It's a lil angsty and is taken a little from 107 but mainly from 503 till 509. Quotes taken from the show as well as a flashback are in italics. Enjoy!

Disclaimer: I don't own Gossip Girl if I did then Blair would be marrying Chuck instead…

The always did say to be careful what you wished for.

Chuck Bass sighed; all he wanted was for her to be happy. Louis's constant struts onto the dark side were making it merely impossible. It's as if he wanted to test him, he actually probably did. He wanted to see if it was still there, the ChuckandBlair that everyone would always speak of in hushed tones. Chuck was not an idiot. In a twisted way he understood why Louis was doing what he was doing. Blair Waldorf was a paragon of all the woman he had ever encountered. He knew what it was like to wonder why she was with him. Why she didn't fall back into Nathanial's broody, stoner arms and get lost in the façade she very much seemed to enjoy. Back when they were young he could never help but be amazed that she would even give him the time of day. He was dark, lecherous, and dangerous, he was Chuck Bass. He couldn't even bring himself to smirk at his own overused tagline.

You know I've got moves.

You were amazing up there.

You sure?

As complicated as it seemed back, then now that he thought about it, it was actually so much simpler. There were no rings involved. Chuck never thought that there would be anything worse his heart could handle than hearing the love of his existence tell him she was getting married to someone else. He was wrong.

I'm pregnant.

There was a part of me that hoped it would be yours.

No, this wasn't Humphrey's misguided attempt to make him feel something. He wished this was Humphrey's doing. He had been trying for what felt like forever, even though it was a mere week to feel something, anything. Paying lowlifes to beat the shit out of him and even accepting what was supposed to be man's best friend into his apartment. Yet, all it took was for her to come to him, the way he knew, even when fighting it, that he wanted her to. Her visit was brief, not even five minutes. She told him the news and when she claimed that she knew having a baby wasn't part of his lifestyle he knew that for her, he would have made it. He would do anything for her. He thought that was made clear when he selflessly gave her up, even when she didn't want him to. Even when he didn't want to. He had despised the apathy even physically; not feeling anything was strange to him. He had wanted to feel. She was indeed all it took, the sight of her, the words she spoke and the scent of her signature Chanel no. 5 she left once she had gone. And then he felt everything. All he could think of was that he hadn't really, truly cried in a long time.

He had to apologise to her. He didn't know what made him decide to do it right that night but he felt a pull towards her that he couldn't ignore. What Dr. Barnes and Louis did to sabotage him was so damn wrong. Like he said, it had done wonders for his trust issues, so he went back to where he learnt the art of trust in the first place. He did want to change it, so there he found himself staring at the tired expression on her face with them both standing in her lounge.

I'm sorry for losing my temper the night you told me Louis proposed to you.

I'm sorry for not waiting longer at the Empire State building.

I'm sorry for treating you like property.

I'm sorry I never told you I loved you when I knew I did.

Most of all I'm sorry I gave up on us when you never did.

He watched her facial expression change and her eyes mist over and he wanted nothing more than to wrap her in him arms and do unspeakable things to her. He couldn't because now they were what they were with her moving on and him trying so hard to let her. She asked him expectantly if that was it and he really did think about it. He could tell her he never should've let her go. He could tell her that she won't marry Louis. He could tell her that he loved her with everything he had in him. He wouldn't though not only because it wouldn't solve anything but because he knew that they both knew it was only just a matter of time. Didn't he once say they were inevitable? So he left her standing there and walked to Harry Winston to return the ring. A ring he held onto so tightly that he got shot for. The ring was her. He couldn't let it go and yet, here he was standing outside a jewellery shop contemplating what letting the ring go would mean. Before he could change his mind he dropped the ring outside the door and walked away. He didn't really know what that meant. Maybe he really was ready to let her go. As promised he did work on himself. He took care of Monkey, he was there for his friends, and he did charity work for Bass Industries. He was making a comeback. A comeback to what exactly he did not know. He soon found out.

He was tested again this time by Blair herself. He couldn't say she didn't know what she was doing. She seemed so hell bent on proving that his goodness was a lie. Her perfect lips. Her scent. Her exposed neck. Damn red hots. Even though Dorota spoke to him he knew what he had to do. He also knew that once he started it word be hard to control himself. She was standing so very close. He knew he had to give in to give her peace of mind. Yet he couldn't help but admit that he gave in for himself too, just a tiny smidge. As soon as it started it was over with a resounding slap. He wouldn't exactly be helping if he told her that she gave in, even if it was for a few seconds so again he let it go. He let her walk away. Again. Even if he let her go, he couldn't say he didn't get a pang in his heart watching her do it.

It was a strange concept to him to think that him and Dan Humphrey were now, dare he say it, friends. It was even worse to think that they were in love with the same woman. Are. He would never have thought he would see the day he would be taken care of anyone let alone Hum Drum Humphrey. You can imagine his surprise when he turned to see Blair standing right in front of him.

You really have changed, haven't you?

"I have. But that shouldn't really matter to you anymore."

"It does."

"Why?"

"Because, I can't help but feel like…never mind. Just forget it."

"Feel like what?"

"What were you going to say?"

"What? When?"

"That night when you came and apologised and I asked you if that was it, you hesitated."

"I did."

"Well? Why did you decide against telling me what you clearly wanted to say before you got that look in your eyes and left?"

"Because I knew then just like I know now that even if I did tell you what I really want to say, it won't change anything."

"How do you know that?"

"Because I know you. I always have and I know that there is a part of you that knows exactly what I was going to say. And even if you don't know, you'll figure it our eventually."

All they did was stare at each other for what felt like ages. Feet both rooted to the ground Chuck couldn't bring himself to go there again and Blair, Blair didn't know what to think. So she sighed before echoing what she had moments before.

"You really have changed haven't you?"

With that, she left.

He really didn't know what to think of his encounter with Blair the previous night. Unfortunately for him he wouldn't have much time to think about that since she walked through his doors once again. She demanded to know how he had changed. He really didn't know what to tell her. Even when they ended up at his psychologists, he still felt as if she was pushing him. She was confusing even him now. Did she want him to tell his so called secret of change because she wanted Louis to be like him, this version of him, the way he was now? Did that mean he was finally becoming the person who she hoped and somehow knew he could be? If that was the case then why was she still pushing? It wasn't supposed to matter anymore so he told her about the ring. How he returned it and he watched her face fall and once again she ran right into the arms of her old friend Denial.

He had to go after her but he had to finish his session first. He couldn't comprehend how or why she would be upset over him returning the ring. It's what she wanted, wasn't it? Or was it her way of knowing that he hadn't given up on them? He didn't know what to think of it. He didn't know what to think of any of it. She definitely through him for a loop when she claimed she was what made him dark. She made him lighter and he felt less of the weight of the world on his shoulders being with her.

He found her lying on her bed flipping through an issue of French Vogue when he entered her room. All he could think is that she was so beautiful he couldn't stand it. To think she was finally all his with no complications. No Nate, no creepy Uncle Jack, just the two of them. He sighed in contentment and without even looking up she spoke.

"Are you going to say anything or just stare at me all day?"

"I'm planning to do much more than stare, no words required."

"Is that so?"

"Oh you know it Waldorf." He said with that infamous smirk gracing his features. He walked up to her and stroked her face intimately before giving her a kiss. This time she sighed in content pulling him closer griping at his shirt. They seemed to melt into each other in every way and one thing led to another. They now both lay on her bed dishevelled appearances and all and then he spoke.

"Have dinner with me." It wasn't a question but more of a demand. Blair just smiled.

"Okay."

"Good," he said putting his clothes back on,"I'll be back in an hour." She merely raised an eyebrow and he walked out the door. He never thought he would ever take a girl out on a date but here he was asking none other than Blair Waldorf on a date. He was so damn lucky she forgave him he didn't even want to imagine what he would do without her. He put his broody thoughts away and dressed in his favourite black Armani suit, tailored to perfection. He wore a white shirt, red tie and blue pocket square with shiny black, Italian shoes. With his swagger intact (as always) he walked out the door and as promised he arrived in Blair's room an hour later. She turned to face him and once again he couldn't help but stare at her again. She was in a red Valentino dress that hugged her curves in all the right places. While it seemed more conservative in the front, it dipped towards her lower back from behind the dress. Her hair was pulled up into a chignon. Chuck let out a breath he didn't know he had been holding.

"You look breath taking." She couldn't help but blush at the way he was looking at her. He made her feel all sorts of things.

"You don't look so bad yourself." She said with a smirk of her own.

"Is that so?" he echoed from earlier while stepping closer to her. Her reply was pressing her lips to his. Once they got started they never could seem to stop. They were both insatiable and- never did make it to dinner.

Chuck shook his head from the memory. He couldn't for the life of him understand how she could think that she, someone so perfect and so….Blair could ever be capable of making him dark was beyond his comprehension so he tried to explain it to her. All of it.

I only want you to be happy, I'm just sorry that it couldn't be with me.

It was like he was letting her go all over again. It seemed to be harder every time. Like there was a knife being pushed deeper and deeper into his soul just when he thought he had started to pull it out.

I'm not the groom.

He walked away this time. He had to. She had to let him go. He had to let her go. He thought he did but sometimes, she would give him that look or be affected by what he said and he just didn't know anymore. He wanted to feel and he wanted her for himself but most of all he wanted her to be happy.

You still love her huh.

I can't imagine a time when I won't.

Like they say be careful what you wish for.

A/N: Hope u liked don't be shy. Reviews=LOVE