The Sixteen Year Old Virgin



Sixteen Year Old Virgin is the 15th episode of Season 3 of Gossip Girl.

Summary
Jenny contemplates losing her virginity to Damien and talks to Serena about it, who thinks that Jenny should wait because it's a huge deal. Serena mentions that she wished she had waited for someone special and that Damien might not be good for her. When she and Nate decide to test Damien, he does stay faithful to Jenny. But Nate, concerned for Jenny, decides to tell Rufus who drags her to Lily's party so that she won't be alone.

She and Damien find each other and go to a hotel room. When Damien dismisses Jenny's virginity, she refuses to have sex with him and Damien breaks up with her. She tells everyone that she is no longer a virgin and that she and Damien had sex; she acts like it's not a big deal.

When Chuck is hit with sexual harassment suits, he decides to hand over the rights to the hotel to Elizabeth where she can temporarily take control until the scandals blow over. It turns out that she was conspiring with Jack and Chuck's lawyer to take control of the Empire Hotel.

Main Characters

 * Blake Lively as Serena van der Woodsen
 * Leighton Meester as Blair Waldorf
 * Penn Badgley as Dan Humphrey
 * Chace Crawford as Nate Archibald
 * Taylor Momsen as Jenny Humphrey
 * Ed Westwick as Chuck Bass
 * Jessica Szohr as Vanessa Abrams
 * Kelly Rutherford as Lily van der Woodsen
 * Matthew Settle as Rufus Humphrey