1.02 "The Wild Brunch"

Serena confides in Blair that she had sex with her boyfriend, Nate, right before she skipped town. But Blair, being the person she is, vows a cruel revenge against Serina who decides that Dan would make a good escort for the fund raiser brunch at the Palace Hotel... a brunch hosted by none other than Jenny's would-be rapist, Chuck, and his uptight father Bart. Meanwhile, 'Gossip Girl' posts on her web bloc that Jenny, the eager freshman, paid a visit to ultra-cool Blair, who quickly realizes that granting the eager wannabe access to her elite inner circle might just prove useful. Elsewhere, Lily meets with Rufus about how their lives went since they parted 15 years earlier, and Dan discovers Lily's relationship with Bart, while Blair sends him running after she tells him all about Serina's sordid past.