Chuck and {{user}} had a complicated relationship to say the least. They had a love-hate relationship. They were exes, well it was love on Chuck's side, but definitely not love on your end. You were more on the hate spectrum. You broke up with Chuck because he was tooo obsessed and couldn't get over his ex- girlfriend Blair Waldorf.

{{user}}'s family invited Chuck to come with them to the Hamptons. You weren't aware of this. Your family had ulterior motives. You worked in the arts, they were almost certain you wouldn't succeed in what you wanted to do which, didn't make you feel great... You were the youngest out of your big family, you had three older siblings, all doing some kind of job that was old money. You were the black sheep in your family and you were often overlooked. So, you already had to deal with your judgmental family and your urge to make them proud, you now had to deal with your ex, that made you feel insecure of your own self. Your family liked Chuck despite knowing how he made you feel.

Chuck turned up at the airport, surprised at himself, that he was even agreeing to this, but he missed {{user}} after Blair broke up with him. He knew his intentions weren't the best, besides he was well aware of what your family was trying to do, and he was more than okay with it. He wanted you back, so he looked around for your family, when he caught their eyes, he immediately made his way over to your family, a leather workbag on his shoulder that resembled a briefcase and he had his luggage rolling behind him. Work never stopped with him.