In the second-season opener, summer in the Hamptons winds down as Serena and Nate carry on a cover-up scheme to make others think they're dating. Meanwhile, Blair returns with a new guy she met abroad, arousing jealousy in Chuck; Dan takes a break from his internship with an author (Jay McInerney) to visit Serena; and Eric introduces Jenny to socialite Tinsley Mortimer at an elite Hamptons party.
Blair is ecstatic to have a royal beau, but a scheming Chuck is not pleased with this development. Meanwhile, Serena and Dan keep their rekindled romance a secret; and Nate learns there are drawbacks to having a May-December romance with a married woman (Madchen Amick). Marcus: Patrick Heusinger.
During a citywide blackout, Dan and Serena get to the heart of their problems while trapped in an elevator. Meanwhile, Blair fears her relationship with Marcus lacks passion; Nate is torn between Vanessa and Catherine; and Eleanor overhears Jenny criticizing one of her designs.
When Dan starts getting friendly with new girl Amanda (Laura-Leigh), Blair carries out a sabotage plan while simultaneously helping Vanessa devise a scheme concerning a secret Catherine's been harboring. Elsewhere, Lily finds it hard to stay away from Rufus.
Eleanor gives Serena and her new socialite friend, Poppy Lifton (Tamara Feldman), front-row seats to her Fashion Week show, and this infuriates Blair. Elsewhere, Dan takes a walk on the wild side and tags along with Chuck, and Lily discovers a secret of Bart's. Designer Michael Kors has a cameo.
The gang visits Yale, Blair's dream school, and Serena suddenly takes an interest in the university just to annoy Blair. While on campus, Dan discovers his recommendation letters weren't submitted; Chuck gets kidnapped by some Skull and Bones members; and Nate gets friendly with a female student.
Vanessa blackmails Blair, so Blair retaliates by asking Chuck to seduce Vanessa. Elsewhere, Bart and Lily's lavish housewarming party requires everyone to be on their best behavior, but Serena doesn't want to play along; and Dan and Jenny uncover a secret of Nate's.
Jenny becomes friends with Agnes (Willa Holland), a model who motivates her to live life on the edge and stand up for herself at work. Meanwhile, Serena also meets someone new, an artist named Aaron Rose (John Patrick Amedori), and the two of them click right away; and Blair tries to seduce Chuck but is surprised to find she's facing an uphill battle.
Jenny and Agnes plan an unconventional fashion show that could make or break Jenny's career. Meanwhile, Blair tries to improve her standing with Yale by babysitting the teenage daughter of a prominent Yale donor.
Blair dislikes Eleanor's new boyfriend, Cyrus Rose (Wallace Shawn), so she sets out to break them up. Meanwhile, Jenny moves in with Agnes; Serena learns something about Aaron that could be a deal breaker; and Dan plans to write an exposé on Bart, which gets him on Chuck's bad side once again. Cyndi Lauper makes a cameo appearance.
Cyrus implements changes to the Waldorf Thanksgiving traditions, which upsets Blair. Meanwhile, Lily tries to play peacemaker with Rufus and Jenny; Chuck and Vanessa help Nate deal with his father; Serena hesitates to open up to Aaron about her past; and Eric uncovers a secret Bart is keeping.
Chuck and Blair make a bet that they can find perfect dates for each other for the Snowflake Ball. Meanwhile, Aaron's ex-girlfriend takes a liking to Dan, and things get complicated with Jenny, Nate and Vanessa.
A tragedy occurs that affects several families.
Chuck's uncle Jack (Desmond Harrington) arrives in town to help his grieving nephew, who's been missing since Bart's funeral. Meanwhile, Blair tries to get accepted into a distinguished ladies club, and Jenny returns to school, ready to take on Penelope and her crew.
Chuck and Jack learn the outcome of Bart's will. Meanwhile, Rufus and Lily inquire about their child, and Dan does his best to keep Rufus and Lily's secret.
As news arrives regarding who has been granted early admission to Yale, Serena connects with her new Shakespeare teacher (Laura Breckenridge), while Blair, upon receiving her first B, does not Meanwhile, Chuck finds an ally in his feud with Jack, and Nate and Vanessa attend the opera.
Blair plots against her least favorite teacher, Rachel. Meanwhile, Chuck wakes up in a hotel with only vague memories of the night before, so Nate and Vanessa try to help him piece things together.
The seniors put on a play, and Serena becomes attracted to the director. Elsewhere, Blair gets crushing news about her future; Dan and Rachel try to stay away from one another; and Chuck seeks help from his adversary, Carter Baizen (Sebastian Stan). Julian: Harmon Walsh.
Spurred by recent changes in her life, Blair seeks out a wilder lifestyle, and this worries Chuck and Serena. Meanwhile, Vanessa suggests that Nate make amends with the Vanderbilts, and Lily and Rufus make lists of their past lovers.
Serena throws Jenny a sweet-16 party, but things get out of hand when Poppy Lifton takes control of the festivities. Elsewhere, Vanessa assists Chuck with a scheme involving Blair and Nate, and Rufus looks for a way to fund Dan's education at Yale when he discovers financial aid is not an option.
Serena returns from her adventure in Spain, and Blair makes a secret pact with Nate's grandfather. Nate, meanwhile, uncovers something about the Captain's arrest, and Dan gets a catering job but is not pleased when he realizes he has to serve his friends during a Seder at the Waldorfs' place.
A changed Georgina (Michelle Trachtenberg) returns to town. Meanwhile, Chuck and Nate's rivalry for Blair's affections puts their friendship in jeopardy again, and things continue to grow complicated for Serena and Gabriel.
Blair plays on Georgina's guilt over her checkered past and ropes her into helping with a scheme. Meanwhile, Chuck and Nate's competition over Blair heats up, and Lily finds a covert way to assist with Dan's college tuition.
Lily flashes back to her teen years in the '80s, recalling the time she was thrown out of boarding school and reconnected with her family in L.A. Elsewhere, Nate and Blair's prom is less than perfect, and Serena and Lily argue about Serena's arrest. No Doubt portray an '80s band. Teenage Lily: Brittany Snow. Rick Rhodes: Andrew McCarthy. Cece Rhodes: Cynthia Watros. Carol Rhodes: Krysten Ritter.
In the second-season finale, a scandalous e-mail is sent out by Gossip Girl as the gang's high-school graduation ceremony takes place, prompting Serena to retaliate. Elsewhere, the mean girls dare Jenny to try to claim the Queen Bee throne; and Lily and Rufus attempt to fix their relationship.