Gossip Girl(2007)

Gossip Girl heads to the Hamptons as summer comes to a close. Guest stars include author JAY McINERNEY (Bright Lights, Big City), socialite TINSLEY MORTIMER and MADCHEN AMICK.

Blair is over the moon to be dating royalty and has every intention of becoming a royal herself, but a scheming Chuck has other plans for Blair and her new love, Marcus (recurring guest star PATRICK HEUSINGER). Serena and Dan agree to keep their recent hookups a secret from their friends and family until they figure out what it means for their relationship. Meanwhile, Nate learns the downside to having an affair with a hot older woman, Catherine (recurring guest star MADCHEN AMICK), who is married.

Serena and Dan are forced to deal with their unspoken problems while trapped in an elevator during a citywide blackout. In a humorous twist, Blair questions the lack of passion in her relationship with Marcus (recurring guest star PATRICK HEUSINGER), while, at the same time, Chuck appears to have lost his "passion" for any woman other than Blair. Meanwhile, Nate struggles between his feelings for Vanessa and his more-complicated-by-the-day relationship with Catherine (recurring guest star MADCHEN AMICK). Plus, Jenny risks losing her internship when Eleanor (recurring guest star MARGARET COLIN) catches Jenny critiquing one of the Eleanor Waldorf designs.

When Serena notices that Dan has been cozying up to the new girl in school, Amanda (guest star LAURA-LEIGH), the ever-loyal Blair and her minions decide to befriend Amanda and sabotage her budding new romance with "lonely boy." Plus, Vanessa discovers a scandalous secret about Catherine (recurring guest star MADCHEN AMICK) and enlists Blair's scheming expertise to use the information to help Nate. Meanwhile, Lily finds herself drawn back to her ex, Rufus, once again.

Blair decides to sabotage her mother's show at Fashion Week. Dan starts hanging out with Chuck, and learns the hard way that a walk on the dark side always has its risks. Designer MICHAEL KORS and socialites TINSLEY MORTIMER and CRISTINA CUOMO make cameo appearances at Eleanor Waldorf's show.

After a fight, Serena wants to get even with Blair -- who dreams of attending Yale University -- and accepts an invitation to visit. Chuck is kidnapped by an elite secret society.

Blair seeks revenge by enticing Chuck to seduce Vanessa. Serena rebels at an important party of Lily's. And Dan and Jenny find out a secret Nate has been hiding from his friends.

Jenny befriends a model (WILLA HOLLAND - "The O.C."), and is encouraged to explore her wild side. Serena is attracted to an artist, Aaron Rose (JOHN PATRICK AMEDORI - "Vanished").

Serena realizes Aaron (JOHN PATRICK AMEDORI) has kept a secret from her. Jenny and Agnes (WILLA HOLLAND) plan a guerilla fashion show. Blair babysits the daughter of a Yale donor.

Dan tries to get close to Bart Bass (recurring guest star ROBERT JOHN BURKE) to possibly write an exposé, but things get heated when Chuck finds out. WALLACE SHAWN guest stars.

Blair's favorite Thanksgiving traditions are ruined by her mother's new boyfriend (WALLACE SHAWN). Serena doesn't tell Aaron (JOHN PATRICK AMEDORI) about her past -- but Dan does.

At the annual Snowflake Ball, Blair and Chuck bet they can find ideal dates for each other. Aaron's (JOHN PATRICK AMEDORI) ex-girlfriend (NATALIE KNEPP) shows interest in Dan.

A sudden and tragic event impacts the lives of everyone.

Chuck's uncle, Jack Bass (recurring guest star DESMOND HARRINGTON - "Dexter," "Rescue Me") arrives on the scene. Meanwhile, Jenny returns to school and takes on the mean girls.

Bart's will is read and everyone learns the fate of the Bass empire. Plus, Dan discovers the secret between Rufus and Lily, and must decide what to do with the information.

Which students will be accepted to Yale University? Plus, Chuck pairs up with an unlikely ally in his war with Jack (recurring guest star DESMOND HARRINGTON) over Bass Industries.

Blair comes up with a plan to get revenge on her teacher, Rachel (LAURA BRECKENRIDGE). Chuck wakes up in a hotel and tries to piece together what happened the night before.

The seniors put on a production of "The Age of Innocence." Chuck enlists help from an unlikely source -- his nemesis, Carter Baizen (SEBASTIAN STAN - "Kings," "The Covenant").

Devastated by the recent plot twist in her life, Blair turns her back on her predictable existence in favor of a wilder lifestyle, causing Serena and Chuck to be concerned.

Serena throws Jenny a party for her 16th birthday, but things get way out of control when Poppy Lifton (TAMARA FELDMAN) turns the small gathering into a huge social event.

Serena returns from her trip to Spain with Poppy (recurring guest star TAMARA FELDMAN) and Gabriel (recurring guest star ARMIE HAMMER). Blair makes a secret deal with Nate's grandfather, William (recurring guest star JAMES NAUGHTON - "The Devil Wears Prada"), and Nate learns some disturbing information about his father's arrest. Meanwhile, Dan 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, where several of his friends and family will be guests.

Georgina (recurring guest star MICHELLE TRACHTENBERG) returns to the Upper East Side after undergoing a major transformation. Chuck and Nate find themselves at a major crossroads in their friendship, a result of their mutual interest in Blair. And Serena finds her relationship with Gabriel (recurring guest star ARMIE HAMMER) growing more complicated.

Blair pressures Georgina (recurring guest star MICHELLE TRACHTENBERG) to help her in a scheme to make amends for her past bad behavior. The rivalry between Nate and Chuck over Blair comes to a head. And Lily hatches a secret plan to help Rufus with Dan's college tuition.

In a special flashback to the 1980s, before she became Lily van der Woodsen, 17-year-old Lily Rhodes (guest star BRITTANY SNOW - "American Dreams," "Hairpray") is kicked out of boarding school and runs away to Los Angeles to reconnect with her parents, Rick (guest star ANDREW McCARTHY - "Lipstick Jungle," "Pretty in Pink") and CeCe (guest star CYNTHIA WATROS - "Lost"), and her older sister, Carol (guest star KRYSTEN RITTER - "Confessions of a Shopaholic"). Plus, NO DOUBT performs as an eighties band called Snowed Out. Back in present day New York City, Blair and Nate attend the prom together, but the evening doesn't turn out exactly as planned -- something Chuck may have a little to do with. And Serena and Lily don't see eye to eye over Serena's recent run-in with the law. Recurring guest star MICHELLE TRACHTENBERG appears as Georgina.

At the Constance Billard and St. Jude graduations, Gossip Girl livens things up by sending out a shocking and damaging email blast in the midst of the commencement ceremony, stirring Serena to come up with a plan of attack. The Mean Girls (recurring guest stars YIN CHANG, NICOLE FISCELLA, AMANDA SETTON and DREAMA WALKER) challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year, and Lily and Rufus struggle to repair their relationship after Lily's betrayal. Plus, the season finale is rife with cliffhangers: Blair and Chuck finally ... Serena is shocked by ... Georgina (recurring guest star MICHELLE TRACHTENBERG) decides to ... And Dan, Nate and Vanessa unknowingly .... OMG!