Serena (Blake Lively) returns from her trip to Spain with Poppy (guest star Tamara Feldman) and Gabriel (guest star Armie Hammer). Blair (Leighton Meester) makes a secret deal with Nate's (Chace Crawford) grandfather, William (guest star James Naughton), and Nate learns some disturbing information about his father's arrest. Dan (Penn Badgley) takes a job as a cater-waiter to earn money for college, but is distressed when he discovers the gig is a Passover seder at the Waldorf penthouse and several of his friends and family are guests.