Episode: 25 Air date: 2009-05-18 Videos: 0
Episode: 18 Air date: 2009-03-16 Videos: 5
The Constance Billard and St. Jude seniors put on a production of "The Age of Innocence" and find their personal lives mirroring conflicts in the play. Serena (Blake Lively) develops a crush on the play's director, Julian (guest star Harmon Walsh), and enlists Vanessa's (Jessica Szohr) knowledge of theater to help her get the otherwise uninterested guys attention. Blair (Leighton Meester) receives devastating news about her future that leads her on a witch-hunt for the person responsible. Dan (Penn Badgley) and Rachel (guest star Laura Breckenridge) agree to stay away from each other in the aftermath of being discovered as more than teacher and student, but find it impossible to keep that promise. Chuck (Ed Westwick) enlists help from an unlikely source, his nemesis Carter Baizen (guest star Sebastian Stan).
Episode: 11 Air date: 2008-11-17 Videos: 3
Thanksgiving in the Waldorf household finds Blair (Leighton Meester) upset that her mom's (Margaret Colin) new boyfriend, Cyrus (guest star Wallace Shawn), has decided to ruin all her favorite traditions, but that's nothing compared to what's coming next. Lily (Kelly Rutherford) finds herself trying to broker a peace treaty between Rufus (Matthew Settle) and Jenny (Taylor Momsen) who is prepared to cut off all communication with her father if she doesn't get her way. Serena (Blake Lively) isn't quite ready to come clean with Aaron (guest star John Patrick Amedori) about her complicated past, but Dan (Penn Badgley) ends up accidentally revealing a few tidbits of his own. Blair and Chuck (Ed Westwick) come to their friend's aid when Nate (Chace Crawford) is once again forced to confront his father's (guest star Sam Robards) abandonment. Finally, Eric (Connor Paolo) discovers a secret that Bart (Robert John Burke) has been keeping from Lily.
Episode: 10 Air date: 2008-11-10 Videos: 3
Blair (Leighton Meester) does not approve of the new man, Cyrus Rose (guest star Wallace Shawn), in her mother's (guest star Margaret Colin) life, so she makes it her mission to break up the lovebirds by any means necessary. Jenny (Taylor Momsen) moves in with Agnes (guest star Willa Holland) as the friends move forward with their plans for a fashion line. Serena (Blake Lively) continues to fall for the new guy in her life, Aaron (guest star John Patrick Amedori), but she learns something about him that threatens to end things just as they are getting really good. Dan (Penn Badgley) decides to win the trust of Bart Bass (guest star Robert John Burke) in order to learn more about the man and possibly write an expose on him for Vanity Fair, but things get heated after Chuck (Ed Westwick) finds out the real reason Dan is spending so much time around his family.