Season 1, Episode 5: “Dare Devil”

Originally aired: October 17, 2007
Writer: Lenn K. Rosenfeld
Director: Jamie Babbit

After his plan bombed, Dan takes Serena to a real “Humphrey” date in which they enjoy until Lily calls him to tell to her that Eric went missing — who was actually bailed out by Blair and Jenny, part of an intense game of truth or dare. The couple finds the three of them and return Eric to the treatment center, only to be brought back home by Lily. Meanwhile, Jenny’s cunning prevents her from being arrested, still part of Blair’s game which causes Blair to give her respect.