MONDAY, JULY 19
"GOSSIP GIRL" - (9:00-10:00 p.m. ET)
"The Sixteen Year Old Virgin" (TV-14, DLS) (HDTV)
DAMIEN PRESSURES JENNY TO SLEEP WITH HIM - Despite being grounded, Jenny (Taylor Momsen) continues to see Damien (guest star Kevin Zeggers) who tells Jenny that he wants to have sex with her. Lily (Kelly Rutherford) tells Rufus (Matthew Settle) the big secret she has been keeping from him even though she knows it's a huge risk. Dan (Penn Badgley) and Vanessa (Jessica Szohr) explore a new stage of their friendship. Chuck (Ed Westwick) is forced to make an extremely difficult decision about his hotel. Blake Lively, Leighton Meester and Chace Crawford also star. Wendy Stanzler directed the episode written by Leila Gerstein (#315).