I do not own Gossip Girl or any of the characters mentioned here.

Chapter 1:

Dan Humphrey sat at his desk typing a short story for English class. Twelfth grade Advanced English had proven to be a difficult to for most of his classmates, but not him. Writing came most naturally to Dan and he had been doing a lot of it lately after his recent breakup with Serena. It had been his decision to call it quits, but that didn't stop him from feeling lonely. He didn't realize by breaking up with Serena meant that no one would speak to him.

That is, except for Nate, who tried his best to remain in contact with Dan, despite his obvious history with Serena. Throughout his on and off relationship with Serena, Dan never felt judged by Nate because he knew that Nate respected him and understood his situation. Dan always admired Nate for that and he had promised himself that he would base one of his characters in his next story on him. He sighed, minimizing his screen and opening his chat.

Dan scanned his AIM list. Nelly Yuki and Jenny Humphrey were the names that stood out. He scratched his curly head trying to decide who he'd torture today.

If he spoke to Nelly she would assume that Dan had ulterior motives in speaking with her and spin their conversation so she could send something to Gossip Girl.

Talking to Jenny would be pointless because

A) If he wanted to do that he could just walk less than twenty steps

and

B) She would probably ignore him anyway.

Just as Dan was about to sign offline, when he saw a little bubble pop up that read: "Blair Waldorf has just signed on." He paused, not remembering ever adding her, but figuring it had probably been Serena who had done it the last time they studied together at the cafe.

Dan drummed his fingers on the desk wondering if messaging her was even worth it. "Couldn't hurt," He thought to himself. Dan quickly typed a message and waited patiently for her response.

Dan Humphrey: Hey I know you probably only have me as a contact because of Serena but do you mind answering a school related question for me?

Blair Waldorf: Normally I would say no but since I do not have to have any actual interaction with you. I guess could, but make it quick Humphrey. I have a lot of work to do.

He half grinned at her comment as he thought of a question to ask her.

Dan Humphrey: Well, don't worry I just wanted to know when our first assignment was due? I only started yesterday because I was away at a soccer game when it was assigned.

Blair Waldorf: Well Humphrey, if you were on top of your work like me, you would know that it isn't due until next week.

Dan Humphrey: Really? Thank God. I still have some time.

He waited for a minute, wondering if he should say anything else. Without thinking, he was typing again.

Dan Humphrey: So, how are you?

Blair Waldorf: Humphrey, I have no time for your questions. Like I told you before, I have a lot of work to do.

Dan Humphrey: Oh right! Sorry.

Blair Waldorf: I'm sorry Brooklyn, I don't mean to take it out on you. I've just been really stressed out lately.

Dan Humphrey: Don't worry about it Waldorf, I understand.

Dan Humphrey: Also I don't know what it is stressing you out, but if it is ever school related, I'm sure I could help you.:)

Dan typed out his cell phone number, surprising himself with his sudden kindness towards Blair Waldorf.

Blair Waldorf: Oh don't worry Daniel, I'm still going to be top of the class. But thank you.

Blair Waldorf: Actually, do you think I could call you right now? I need some input on an English essay, if you're free?

He was surprised that she was so willing to ask for his help but he knew better than to think too much of it.

Dan Humphrey: Sure I'm free, just send it to me and we'll discuss it over the phone?

Dan's phone rang and he felt a sudden kind of uncertainty talking to Serena's not so friendly best friend.

It wasn't that Dan disliked her, it was just her snobbish attitude that put him off from associating with her. That and her distaste from all things Brooklyn, including himself. Still, he figured it was too late to just ignore her call.

"Waldorf." He said, coolly as he pressed talk.

"Listen Humphrey I am in need of some proper input and as Serena has mentioned to me before, you're not the worst person when it comes to writing." She spoke quick but with authority.

Dan opened his mouth to speak but was cut off by her the sound of her voice.

"I read your piece in the school paper and it was... insightful and surprisingly, not as terrible as I thought it would be."

Dan chuckled a little. "Well, that almost sounded like a compliment Waldorf." He opened his email and saw he had just received a file attachment from Blair. "Before I open this, tell me about what the topic of your essay is?"

He heard Blair take a deep breath. "My teacher asked us to pick a topic that we cared about, so naturally I chose gender equality."

Dan found himself smiling, unsurpassed at her answer. "Okay well I-."

He heard a door open and a woman began yelling on the other end. at Blair. "Blair Cornelia Waldorf I called you down to eat almost an hour ago. Don't think I haven't noticed you've been losing weig-."

He heard a beeping noise and pulled the phone away from his ear. She had hung up on him. Dan set his phone down, figuring she'd text him to explain what happened, or so he thought. For the first time in his life, Dan worried about Blair Waldorf and for the rest of the night, he was not able to shake what he had heard.

a/n Well I know this is short but this is this something I randomly thought of while watching some fanvids the other day. I'm not too sure where I'm going with this or if I'll even continue it, but I'd really appreciate feedback. So if you could please read and review?