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.
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.
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.
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.
A sudden and tragic event impacts the lives of everyone.
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.
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.
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.
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.
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").
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.
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 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 Tionsley Mortimer and Cristina Cuomo make cameo appearances at Eleanor Waldorf's show.
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.
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.
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.