Ben’s (guest star David Call) mother (guest star Marsha Dietlein Bennett) comes to town, forcing issues to the surface between Ben and Serena. Russell Thorpe (guest star Michael Boatman) is determined to destroy Chuck’s family legacy, but he risks alienating his daughter, Raina (guest star Tika Sumpter), in the process. Billy Baldwin returns as William van der Woodsen, Lily’s ex-husband and Serena... More >

Eric turns 18; Blair stretches herself too thin; Serena must choose between Ben and her family; Lily and Chuck's relationship remains icy.

Chuck makes one last attempt to save his family's company; Blair is given a challenging assignment and the promise of a possible promotion; Serena grapples with her feelings for Ben.

Blair asks Nate to help her gain favor with her high-strung boss; Damien (Kevin Zegers) causes more trouble; Chuck is torn between business and pleasure.

Blair's excitement at landing an internship is dampened when she discovers Dan did too; Chuck meets his match in Russell Thorpe; Nate gets news about his father's business prospects.

One of Bart Bass' former associates (Michael Boatman) and his daughter Raina (Tika Sumpter) return to Manhattan; Chuck and Serena unite against Lily; Nate worries his father isn't taking his parole seriously.

Jenny is tempted by a once-in-a-lifetime chance to meet Tim Gunn; Serena discovers something about her new boyfriend.

A damaging rumor about Serena is started; a mysterious student thwarts Blair's plans to secure a job as a powerful businesswoman's assistant.

Nate decides to confront Juliet when he thinks she is keeping a secret from him; Blair tries to undermine Chuck's newfound happiness; Dan is torn between his feelings for Serena and Vanessa.

Blair is in for a few big surprises on her first day at Columbia; Serena becomes suspicious of Juliet (Katie Cassidy); worried about Dan, Rufus decides to take matters into his own hands.

Chuck arrives in Paris with a beautiful new woman; Serena tries to avoid a decision; an intriguing woman helps Nate come to a realization; Dan's drama with Georgina continues.