Season 1 - Episode 12

12 - School Lies
Impromptu party at the school's swimming pool. Serena, Blair, Nate, Chuck and their entourage break into the school swimming pool for a night of fun, but when a member of their group nearly drowns, the school threatens to expel the person responsible for the break-in. Everyone agrees to keep a secret pact and say nothing, but it ultimately creates major tension between Serena and Dan, who isn't sure he's ready to take the fall for someone else and risk his future. Vanessa is working on a documentary project about private schools and accidentally captures Blair and Chuck discussing their affair. Lily contemplates telling Rufus how she really feels about him.

Season 1 - Episode 11

11 - Roman Holiday
Harold tells Blair that he and his boyfriend Roman bought a vineyard in France. Blair freaks a bit because she finds it too permanent. Eleanor hits it off with Jack Roth, a wealthy businessman in his 50s. Blair feels sad because the day she envisioned spending with her father doesn't turn how she thought it would. Rufus faces off a man named Alex who is hitting on his wife. Serena is shocked when Lily announces she is dating Bart Bass.

Season 1 - Episode 10

10 - Hi Society
Serena's grandmother has much to say about the upcoming debutante ball, insisting that her reluctant granddaughter attend - and find a more suitable escort than Dan. Meanwhile, Nate accompanies Blair to the ball as her friend and wants to find out if Blair is seeing someone else. Jenny also hopes to go to the upper-class event - her parents would rather she didn't, however that doesn't stop her.