Nate (Chace Crawford) and Serena (Blake Lively) decide to explore the boundaries of their friendship. Blair (Leighton Meester) suspects that Chuck (Ed Westwick) is having problems forgetting about the woman (guest star Laura Harring) he saw at his father's grave. Jenny (Taylor Momsen) agrees to accompany Damien (guest star Kevin Zegers) to a State Dinner but is unaware that he needs her help with a drug exchange. Vanessa (Jessica Szohr) and Dan (Penn Badgley) attempt to move past the awkwardness of Dan's confession of love. Rufus (Matthew Settle) returns from a ski trip and tries his best to avoid Lily (Kelly Rutherford).