“Blair Waldorf Must Pie,” Season 1, Episode 9 Very different experiences from when I was a sophomore in high school but an episode to remember. So into it that she loses her virginity to him in the back of his limo. Then Blair is very into Chuck being into it. While he's there, Blair gets over her breakup with Nate by letting it all go on the burlesque stage–and Chuck's into it. Bart Bass is interested in buying a burlesque club, so he sends his sophomore-in-highschool son to go check it out. The episode where Chuck and Blair's romance officially began. It also introduces us to the fact that these sophomores in high school attend parties on weekdays far more than anyone else does, and that their original casting for Eleanor Waldorf was abysmal.
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