The second season of the American teen drama television series Gossip Girl premiered on The CW on September 1, 2008, and concluded on May 18, 2009, consisting of 25 episodes.

The newly formed Bass-Van der Woodsen family is now regarded as the richest in New York's Upper East Side.

As Nate's family issues intensify, he takes extreme measures that ultimately hurt him and his chances with Vanessa Abrams.

Lily van der Woodsen grows closer with Rufus Humphrey, even after her new marriage with Bart Bass.

Serena, Eric, Dan and Jenny learn a long-buried secret from Lily and Rufus' past that has come to light.

While interning for Eleanor Waldorf's company, Jenny sneaks a coveted invite to the Hamptons' White Party and meets socialite Tinsley Mortimer.

Serena and Dan agree to keep their recent hook-ups a secret from their friends and family until they figure out what all this means for their relationship.

Chuck is kidnapped by Skull and Bones members while visiting Yale, and Nate meets a student who may hold the key to Dan's acceptance.

Lily and Bart organize a lavish housewarming celebration and expect their children to make them proud in front of the assembled press, but a rebellious Serena refuses to play by their rules.

Thanksgiving in the Waldorf household finds Blair upset that her mom's new boyfriend, Cyrus, has decided to ruin all her favorite traditions, but that is nothing compared to what is coming next.

Jenny returns to Constance Billard and immediately takes on Penelope and her posse of mean girls, but no one is going down without a valiant Gossip Girl-worthy fight.

Noticing that his father has been acting strangely as of late, Dan does some investigating and uncovers Rufus and Lily's secret, putting him in the awkward situation of deciding what to do with this shocking revelation and whom to share it with.

It is that stressful time of year when Constance Billard and St. Jude's students find out who is and is not worthy of early admission to Yale University.

Serena bonds with her new Shakespeare teacher, Rachel, who has no clue the wrath she is about to suffer after giving Blair the first B of her prep school career.

In retaliation for not playing by the unspoken rules of Constance Billard, Blair hatches a plan to bring down her teacher, Rachel.

After Chuck wakes up in a hotel and only has a minor recollection of what happened the previous evening, Nate and Vanessa try to help him fill in the missing pieces.

Serena develops a crush on the play's director, Julian, and enlists Vanessa's knowledge of theater to help her get his attention.

Dan and Rachel agree to stay away from each other in the aftermath of being discovered as more than teacher and student, but find it impossible to keep that promise, and end up having sex before the show.

Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a more wild lifestyle, causing Serena and Chuck to have serious concerns about her new lover, Carter Baizen.

Rufus learns that Dan will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education.

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 and several of his friends and family are guests.

In a flashback to the 1980s, 17-year-old Lily Rhodes gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her estranged older sister, Carol.

Back in the present day, Blair and Nate attend their senior prom together, but the evening does not turn out exactly as planned due to Chuck's tricks.

Gossip Girl plans to spice things up during the graduating class' final days of high school by spreading a tidal wave of juicy secrets.

With the seniors leaving, Jenny's reputation is up in the air as Blair and her minions decide to choose one incoming Juniors to fill the Queen Bee position.