They had known each other since both of them where young, in kindergarten to be precise. She was his best friend’s girlfriend, and he was a pain and a nuisance to her. Chuck bajo was a notorious among the Upper East Side for hard drinking and women. It was a known fact that he had slept his way through half of the Upper East Side, but there was only one woman he slept with who really mattered to him, only one woman he truly cared for, and only one woman he would ever truly love.

Blair Waldorf, she thought she was in amor with Nate Archibald, her boyfriend since as long as she could remember. Blair and Nate where the perfect couple among the residents of the Upper East Side. They matched each other perfectly in every way possible, until one night when, they had an argument and Serena was out of town, who did Blair turn to for support.....? Chuck Bass.