As Blair decided on her drink, Chuck was inwardly berating himself for revealing any detail of his past. It was unseemly. Granted, he and Blair actually knew a hell of a lot more about each other than either of them probably cared to admit, but even so, Chuck preferred to keep his dirty laundry as private as possible, especially as far as his family was concerned. It was a small detail, yes, but the devil was in the details.
Or, as Chuck liked to think, the real devil was in the absence of them. Little stories about his father, or passing comments about their relationship, only made him look more complex from the outside. The details humanized him, they reminded people that he wasn't just the one-track-minded bastard the majority of the Upper East Side (plus anyone else who read Gossip Girl) thought he was. But growing up rich and powerful and always in the spotlight had taught him that appearing human often caused more problems than it solved. Better to play into Gossip Girl's narrative; better to give the people what they wanted. It was easy to fit into their role. Too easy. Making them believe what they wanted to believe gave him power, and Chuck found it much easier to con them than try to make them understand him.
So, as he prepared the martini, tipping a liberal amount of olive juice into the cup, he smirked and said exactly what anyone would've expected him to say. "I knew you liked it dirty," he teased, passing her the drink and raising his own glass for the earlier toast.
"I don't know," he said honestly, in response to her question. "At the very least I doubt that there'll be school tomorrow, given what happened at the dance. I'm sure Queller will be in contact." He paused, a simultaneously joyous and sickening thought occurring to him. "If she survived."