Gossip Girl (2007): Season 1, Episode 5

1 - 5: Dare Devil

Dan makes elaborate plans to impress Serena on their first official date. The same night, Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high stakes game of "truth or dare." Meanwhile, when Lily discovers that Eric (Connor Paolo) is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus.