Gossip Girl (season 2)

As the summer draws to a close in the Hamptons, Serena and Nate have everyone fooled into thinking they are a couple to cover up the fact that Nate has been hooking up with an older woman. Blair returns from abroad with a hot guy on her arm, Marcus (Patrick Heusinger), making a very jealous Chuck question his decision to leave Blair stranded at the heliport. Dan has spent the summer assisting a famous author (Jay McInerney), and clearly still has one certain girl on his mind, which results in him going after her. While interning for Eleanor Waldorf's company, Jenny sneaks a coveted invite to the Hamptons' white Party at which Eric introduces her to socialite Tinsley Mortimer.

Blair is over the moon that she is 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. 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. Meanwhile, Nate learns the downside to having an affair with a hot older woman, Catherine, who also happens to be married.

In a humorous twist, Blair questions the lack of passion in her relationship with Marcus, 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. Jenny risks losing her internship when Eleanor catches Jenny critiquing one of the Eleanor Waldorf designs. Whilst being stuck in a elevator due to the blackout, Dan and Serena talk about their relationship and come to the conclusion that they are totally two different people and that it will not work out for the two.

School is back in session for the Upper East Siders, and Blair and her minions decide to befriend the new girl Amanda (Laura-Leigh) in order to sabotage her for coming in between Serena and Dan. Vanessa discovers a scandalous secret about Catherine 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.

In the midst of Fashion Week, a furious Blair learns that her mother, Eleanor, at the suggestion of her protégée Jenny, has given Serena and her new socialite friend, Poppy Lifton (Tamara Feldman), front row seats to the Eleanor Waldorf show. Hurt once again by Serena's popularity and her mother's betrayal, Blair decides to sabotage the show. Meanwhile, Dan starts hanging out with Chuck, but a walk on the dark side always has its risks and Dan learns that the hard way. Lily learns a secret that her new husband Bart has been keeping from her.

Absent: Chace Crawford as Nate Archibald.

After Blair and Serena get into a catfight, Serena decides to get even with Blair, who has always dreamed of attending Yale University, by ditching her plans to visit Brown University, and instead accepting the Dean of Yale's personal invitation to visit the school. After discovering that none of his recommendation letters for Yale were ever submitted, Dan frantically tries to figure out a way to salvage his chances of getting into the school. While on the Yale campus, Chuck is kidnapped by members of a secret society, and Nate hooks up with a co-ed.

Vanessa uses the scandalous picture of Catherine and Marcus to blackmail Blair into being a nicer person, so Blair seeks revenge by enticing Chuck to seduce Vanessa. Eric introduces his new boyfriend Jonathan to Serena and Blair. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud in front of the attending press, but a rebellious Serena is not ready to play by their rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

Jenny befriends a young model, Agnes (Willa Holland), who encourages Jenny to not only explore her wild side, but also confront her boss, Eleanor Waldorf, who is attempting to "borrow" Jenny's designs. Serena meets an artist, Aaron Rose (John Patrick Amedori), and realizes they have an instant chemistry. Blair attempts to seduce Chuck, but it proves tougher than she ever imagined.

Serena invites Aaron to be her guest at a charity gala honoring Lily and Bart, but after discovering a secret that Aaron has been keeping from her she begins to question whether Aaron is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair naively agrees to babysit the 15-year-old daughter of a prominent Yale donor, but the teenager proves to be more than a handful and Blair begins to suspect that the evening may actually wind up hurting her chances of getting into the college of her dreams. Meanwhile, Jenny and Agnes plan a guerilla fashion show that will either launch Jenny's star or ruin her chances of ever being accepted by the industry.

Blair does not approve of the new man, Cyrus Rose (Wallace Shawn), in her mother's life, so she makes it her mission to break up the lovebirds by any means necessary. Jenny moves in with Agnes as the friends move forward with their plans for a fashion line. Serena continues to fall for the new guy in her life, Aaron, but she learns something about him that threatens to end things just as they are getting really good. Dan decides to win the trust of Bart Bass in order to learn more about the man and possibly write an exposé on him for Vanity Fair, but things get heated after Chuck finds out the real reason Dan is spending so much time around his family. Singer Cyndi Lauper makes a cameo at Blair's 18th birthday party celebration.

Absent: Chace Crawford as Nate Archibald.

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's nothing compared to what's coming next. Lily finds herself trying to broker a peace treaty between Rufus and Jenny who is prepared to cut off all communication with her father if she does not get her way. Serena is not quite ready to come clean with Aaron about her complicated past, but Dan ends up accidentally revealing a few tidbits of his own. Vanessa and Chuck come to their friend's aid when Nate is once again forced to confront his father's abandonment. Finally, Eric discovers a secret that Bart has been keeping from Lily.

For the annual Snowflake Ball, Blair and Chuck make a bet that they can find the ideal dates for each other. This ends with them finding doppelgängers of themselves. However, while Blair and Chuck leave to talk, the doppelgängers get busy. Blair and Chuck share a moment. Aaron's ex-girlfriend, Lexi (Natalie Knepp), expresses an interest in Dan. There is drama between Serena and Dan about their sex lives. Nate, Jenny and Vanessa get into a tangled situation that puts their friendships and hearts on the line. Vanessa steals a love letter Nate had written to Jenny and continues a relationship with Nate. Jenny retaliates by sending an unsuspecting Vanessa to the ball in a see-through dress. After the ball, Nate ends things with Jenny and goes after Vanessa. As Bart Bass is trying to return to the Snowflake Ball, he suffers a car accident.

A sudden and tragic event hits the Bass family with the passing of Bart Bass. The whole city is shocked, so as Lily. Chuck does not handle very well with the passing of his father. Blair has something important to say to Chuck, but it is said at a bad time. When Serena travels to Argentina with Aaron, Dan decides to express his feelings for her. Meanwhile, Cyrus and Eleanor get married, and Rufus discovers something that Lily has been keeping from everybody for a long time.

With Chuck missing since his father's funeral, Jack (Desmond Harrington) arrives on the Upper East Side to help Chuck pick up the messy pieces, but first he has to find him. Trying her best to forget her last painful exchange with Chuck, Blair focuses her attention on being accepted into the most prestigious ladies club in the city, Colony Club. 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. Meanwhile, after Serena tells Dan about her recent break-up, they decide to get back together.

Absent: Chace Crawford as Nate Archibald.

With the reading of Bart's will, Chuck, Bart's brother, Jack, and Blair learn the fate of the Bass empire. Rufus and Lily's relationship is strained as Rufus seeks details about the child he never knew he had. 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 (Laura Breckenridge), who has no clue the wrath she is about to suffer after giving Blair the first B of her prep school career. Chuck pairs up with an unlikely ally in his war with Jack over Bass Industries. Meanwhile, Nate and Vanessa have a romantic night at the opera.

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. Blair starts a rumor about Dan and Rachel, which gets Rachel fired. Dan and Serena decide to break up and Dan has sex with Rachel, as she is no longer a teacher. Unaware of this, the school reinstates Rachel.

The seniors put on a production of The Age of Innocence and find their personal lives mirroring the play. Serena develops a crush on the play's director, Julian (Harmon Walsh), and enlists Vanessa's knowledge of theater to help her get his attention. Nate has difficulties with the play and the director and his relationship with Vanessa. Blair receives devastating news about her future that leads her on a witch-hunt for the person responsible. Blair thinks it is Dan, but it turns out to be Rachel. 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. Chuck stumbles upon a secret society and is put into a dangerous situation to try and protect his new love interest. Chuck enlists help from an unlikely source, his nemesis Carter Baizen (Sebastian Stan). However, the whole time the girl is using Chuck for his money.

Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a more wild and unpredictable lifestyle, causing Serena and Chuck to have serious concerns about her new lover, Carter. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother's Kennedy-esque family, the Van der Bilts, who abandoned Nate and his mother when they needed them most. In a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.

Serena decides to throw Jenny an intimate party for her 16th birthday, but things get way out of control when Serena turns the small gathering into a party. An angry Jenny writes a post to Gossip Girl, turning the party into a huge social event. In a moment of weakness, Vanessa agrees to help Chuck with a scheme having to do with Blair and Nate. 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. The episode ends with Chuck and Vanessa starting a friends with benefits, and Nate and Blair starting a relationship.

Serena returns from her trip to Spain with Poppy and Gabriel (Armie Hammer). Blair makes a secret deal with Nate's grandfather, William (James Naughton), and Nate learns some disturbing information about his father's arrest. 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.

Georgina Sparks returns to the Upper East Side after undergoing a major transformation. Chuck and Nate find themselves at a major crossroads in their relationship as it pertains to their mutual interest in Blair. Serena finds her relationship with Gabriel growing more complicated.

Blair pressures Georgina into making amends for her past bad behavior by helping her in a scheme. The rivalry between Nate and Chuck over Blair comes to a head. Lily hatches a secret plan to help Rufus with Dan's college tuition.

In a flashback to the 1980s, 17-year-old Lily Rhodes (Brittany Snow) gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick (Andrew McCarthy) and Cece (Cynthia Watros), and sister, Carol (Krysten Ritter). Back in present day, Blair and Nate attend prom together, but the evening does not turn out exactly as planned and Chuck and Serena have a little something to do with that. Serena and Lily do not see eye-to-eye over Serena's recent run-in with the law. No Doubt performs in the flashbacks as a 1980s band called Snowed Out.

Gossip Girl decides to liven things up at the Constance Billard and St. Jude's graduation 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. Lily and Rufus get engaged and move in together. With Blair's blessing, Jenny becomes the new "Queen Bee". Chuck finally admits his love to Blair and the two reconcile. Nate decides to go on the backpacking trip with Vanessa, while Georgina recovers Dan's money and requests Blair for a roommate at New York University. Carter Baizen reveals to Serena where her father is. In the end, Serena is going to Brown, Blair, Dan, Vanessa, and Georgina are going to NYU, and Nate is going to Columbia University.