306: ENOUGH ABOUT EVE airdate: October 19, 2009 directed by: John Stephens written by: Jake Coburn
Vanessa (Jessica Szohr), hoping to finally win her mother Gabriela's (guest star Gina Torres) approval, desperately vies with Blair (Leighton Meester) for the honor of delivering the freshman toast at NYU, but at what price? Dan (Penn Badgley) invites Olivia (guest star Hilary Duff) to meet Rufus (Matthew Settle) and Lily (Kelly Rutherford), which leads to all sorts of problems for the new couple. Serena (Blake Lively) and Nate (Chace Crawford) team up to help Carter Baizen (guest star Sebastian Stan). Taylor Momsen and Ed Westwick also star.
Blair: Are you upset because you kissed a guy? Chuck: I’m upset because I kissed somebody that wasn’t you. Do you really think I’ve never kissed a guy before?
Blair: When will you learn? Some people are simply better than others.
Blair: Generations of breeding and wealth had to come together to produce me. I have more in common with Marie Antoinette than with you.
Blair: I’m in no mood to hear you fawn over some girl with tacky accessories who lives to recycle!
Jenny: Dan, play the parent card. People like you more when they meet our family.
In need of publicity for his new hotel, Chuck (Ed Westwick) decides to move up his club's opening and enlists Serena's (Blake Lively) help to get the word out to her celebrity clients. Feeling left out of the planning, Blair (Leighton Meester) attempts to win Chuck's approval by secretly helping him with a problem concerning opening night. Dan (Penn Badgley) is unnerved when he finally watches one of Olivia's (guest star Hilary Huff) infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson (guest star Simon Miller). Jenny (Taylor Momsen) is forced to choose between her relationship with Eric (Connor Paolo) and her new role as Queen Bee. Rufus (Matthew Settle) gets Lily (Kelly Rutherford) into the Halloween spirit. Chace Crawford also stars. Joe Lazarov directed the episode written by Sara Goodman.