The sun was setting behind him and a warm orange glow flooded through the expansive glass windows of his office. Chuck tried to concentrate on the contracts in front of him, but his mind began to wander. It had been a week since he woke up and found his bed empty. A week since Blair Waldorf agreed to "keep things casual with him" (whatever that meant). A week since he heard from her.

He had learned from Serena at brunch last Sunday that Blair had flown back to London. Apparently she would be flying frequently back and forth between New York and London over the next few months to help Serena with the wedding. Still, being in London didn't mean she couldn't at least text him...it wasn't like this was 1674 and she needed to send him a letter via carrier dove. A simple "hello" text would have been appreciated.

Chuck shook his head as he realized what he was asking for. He was the one to ask her to keep things casual...so then why was he itching for more?

Maybe it was because of how unfinished everything always was between them. Senior year when she threw the peonies at his feet in the elevator after the disastrous brunch, she never even bothered to tell him she was leaving. It was nearly two weeks later after he had pulled himself back together that he noticed he hadn't seen her around school. He had thought about asking his (ex?) step sister about her best friend, but at the time, their relationship was rocky at best.

Luckily for him, as he had returned to the van der Bass home to collect some things, he overheard a conversation between the blonde and brunette.

"Blair, I know you said the spring semester had already started, but did you have to leave so quickly?"

"Yes, I know, but will you at least be back for summer?"

"Ugh, well fine! You know I'll be on the first flight to France as soon as I throw my cap!"

After that his curiosity got the better of him and he asked Andrew, his PI, to keep some tabs on her. I'd learn over the years that she finished her senior year in France with her father and Roman and then attended Cambridge University. After graduating, she had started an interior design firm which catered to the royal family and friends. He never would have thought that after all these years, he'd run into her at Serena and Nate's engagement party and all it would take was three martinis for her to end up in suite 1812 with him again.

Being so lost in his thoughts of Blair and the past, he hardly noticed that he had left his office and was about to climb into his waiting limo. Suddenly though, he noticed someone across the street. It was a busy Friday evening in early December on the upper east side. Everyone was rushing out from work to do some holiday shopping to or attend a Christmas happy hour and yet, it seemed like the streets cleared and time stood still as he stared across the bustling street to see brunette curls bounce as they exited a taxi.

Blair.

She was unmistakable to him even from a distance and he swore her smile brought warmth even in the chilly weather. So she was back for the weekend again, perhaps he could cash in on their arrangement this weekend.

Sadly his happy thoughts were wiped from his mind and the chill returned as he noticed where Blair's smile was directed.

A tall man with sandy brown hair had approached her taxi and extended her arm for him. As she happily accepted and entered the restaurant with him, Chuck had the sinking feeling in his stomach that he had just witnessed the beginning of a date.

He entered his limo not wanting to see anymore and quickly pulled out his phone as Arthur began to pull away from the curb.

"Andrew, yes, I need you to look into something for me. Ms. Blair Waldorf appears to be having dinner with someone tonight at Daniel. Find out everything you can about this dinner and who she is dining with. Also look up her return flight to London." and with that he hung up.

He was definitely not being obsessive over his causal friend with benefits…

Whoo chapter two is up! Sorry for the long delay, I've had a crazy week, but hopefully this gives some background on how they ended up where they are. I know I've mostly written from Chucks POV, but is anyone interested in more Blair POV or should I keep it this way?