Starring

Blake Lively
Serena van der Woodsen

Leighton Meester
Blair Waldorf

Penn Badgley
Dan Humphrey

Chace Crawford
Nate Archibald

Taylor Momsen
Jenny Humphrey

Ed Westwick
Chuck Bass

Jessica Szohr
Vanessa Abrams

Kelly Rutherford
Lily Bass

Matthew Settle
Rufus Humphrey

Kristen Bell
"Gossip Girl"

Season 2

As the summer vacation comes to a close, Blair Waldorf arrives in the Hamptons with James (guest star Patrick Heusinger). Although Blair is uninterested in James and is only using him as a tool to make Chuck jealous, he professes his love and reveals himself to be Marcus Beaton, an English Lord. Blair is interested in his title. Throughout the summer, Serena and Nate lead a fake relationship in order for him to continue an affair with Catherine Mason (guest star Mädchen Amick), a married woman. Blair and Chuck feud over saying that they love each other. They attempt to seduce and destroy Vanessa, however, the night ends with Chuck telling Blair he has chased her long enough and that she must now chase him. Blair attempts to seduce Chuck with the help of Dan, but the attempts prove unsuccessful and the pair are once again faced with the dilemma of saying they love one another. Dan finds out what Chuck and Blair did to Vanessa and gives Blair bad advice, resulting in her decision not to tell Chuck that she loves him. Later, Chuck and Blair decide to wait for the future to be together.

Dan decides to try something out of his comfort-zone so he can write a story, and ends up going to Chuck for help. While Chuck educates him on the "ways of Chuck Bass", Dan defends Chuck and they both go to jail, where Chuck tells Dan how his mother died giving birth to him and how his father hates him for it. He takes this back when he finds out that Dan was using him to write a story. Dan writes the story anyway. Dan finds out that Nate is living in his seized apartment and invites him to live with his family. Meanwhile, Jenny ends up in an internship for Blair's mother, Eleanor Waldorf. However, Eleanor ends up using Jenny and not crediting her for all of her hard work. Agnes, a model for Eleanor, sees this and tells Jenny to quit, which she does, and the two start hanging out as Agnes introduces her to a new crowd of bad influences. She becomes rebellious, wants to start her own clothing line, and she decided she would become emancipated to do it. In the end everything works out for the best.

Frustrated with Bart, Lily and Rufus tell each other at the ball that they still have feelings for each other. Chuck overhears and calls his father, telling him to come immediately to the dance. Bart's limousine is involved in an accident on the way, and he dies.
Lily's mother reveals that Lily and Rufus had a child, although Rufus did not know. Rufus and Lily go off together on a search for their son.

Chuck's uncle Jack Bass (guest star Desmond Harrington) returns and tells Blair he will now take care of Chuck, much to Blair's annoyance. Chuck inherits his father's fortune as well as 51% share of Bass Industries. The Bass Industries chair people witness Chuck in his father's office with a group of prostitutes, and give the company to Jack. Lily is very much unhappy when she hears about Jack Bass's plans for Bass Industries. She hires a lawyer and convinces Chuck to sign papers to make her his legal guardian instead. Chuck decides that he wants to rejoin Lily's family making her the owner of Bass Industries.

Dan and Serena are accepted to Yale, but Blair is wait-listed. Serena learns that if she turns down Yale, Blair will be accepted. Blair, unaware Serena has been accepted to Yale, plots revenge on a new, young teacher, Ms. Carr(guest star Laura Breckenridge), who had recently given her a grade B. When Serena learns this, she reveals to Blair that she has passed on Yale, and that Blair will be accepted. Blair invites the teacher, Ms Carr, to the opera as a prank. The headmistress informs Blair her acceptance to Yale is suspended, and Blair spreads a rumor that Dan and Ms. Carr are in a relationship. Serena becomes suspicious. Blair is discovered to be the rumor's creator, when Nelly confesses to the headmistress, and Blair is expelled.

Serena sees Dan and Ms. Carr in a coffee shop together, and sees Dan intimately comforting Ms. Carr. Serena captures a photo where it is displayed at a PTA meeting, and Ms. Carr is fired and Blair is readmitted to Constance Billard. Dan defends himself, but he and Serena break up. Serena admits to Ms. Carr that she was the one to take the photo. Dan later visits Ms. Carr, where the two kiss and have sex. Meanwhile, the headmistress decides to give Ms. Carr her job back, afraid of negative publicity. Reinstated to her job, however, Ms. Carr decides to take revenge on Blair and calls Yale, telling them she had been given detention for hazing a teacher. Blair's acceptance to Yale is rescinded and given to Nelly instead. Blair tries to find out who called Yale. In the meantime, Dan and Ms. Carr have been carrying on their affair, and have sex in the costume room. But Dan discovers that it was Ms. Carr who ratted Blair out to Yale, and ends things with her, telling Blair that it was Ms. Carr who called Yale. Blair tells Ms. Carr that her punishment will just be to 'live with it'. Ms. Carr leaves a note for Dan telling him she's returning to Iowa.

Chuck is mistakenly invited to a Skull and Bones society meeting by a mistress in place of his father. He becomes obsessed with Elle, the woman who met him there, and attempts to help her flee the country when she tells him she's in trouble. But he finds out that she was just using his money for an escape route, and when she leaves, Chuck goes to Blair's to wait for her there. Meanwhile, Blair sits in a bar drinking alone. Carter Baizen sits next to her and offers to buy her a drink, putting his hand on her knee.

Blair is devastated about what has happened to her life, so she goes to Carter Baizen for help. However, Chuck and Serena realize Carter is encouraging the worst of Blair by letting her loose and changing her to a new Blair. They clear him out, but Blair only gets worse. Vanessa urges Nate to reconnect with his family, despite the fact that they weren't there during his father's financial trouble. The Vanderbilts throw a party for prominent members of NYC society. At the party, Blair goes off the deep end, insulting everyone she meets, getting drunk, and seducing Chuck to no avail, as he says that this isn't the Blair he wants. Finally, everything hits her and she is devastated. Nate finds her crying and comforts her, reminding her that she is Blair Waldorf, someone who doesn't let a mishap get in the way of what she wants. Chuck tells Serena that he is losing her and she said fight for her. When Nate accepts an internship provided by his grandfather instead of going on a summer vacation with Vanessa that they had been planning for a while, she walks out on the party, leaving their relationship in the air. Chuck goes to visit Blair to tell her he loves her but he see's Nate's jacket after Dorota tells him she is asleep.

Serena decides to throw Jenny an intimate party for her sixteenth birthday, but things get way out of control when Poppy Lifton (guest star Tamara Feldman) turns the small gathering 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.

Serena returns from her trip to Spain with Poppy and Gabriel (guest star Armie Hammer). Blair makes a secret deal with Nate's grandfather, William (guest star 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 and he has to soon lie to cover up his actions.

Georgina Spark (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 relationship as it pertains to their mutual interest in Blair, he tells Chuck to man-up and tell Blair how he feels otherwise let her go. Serena finds her relationship with Gabriel growing more complicated by the day as she finds out he may have been involved with a scam to steal money from investors including Rufus, who invested Dan's college tuition money with him. Nate asks Blair to move in with him.

Blair pressures Georgina into making amends for her past bad behavior by helping her in a scheme to get the money back from Poppy. 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 an effort to protect Serena's reputation, Lily puts Serena in jail for stealing a bracelet. Blair asks Chuck if he loves her or whether its just a game and he says it is just a game. Serena overhears and asked why he said that, and he says it was because he loves her, but can't make her happy.

In a flashback to the 80s, 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, and the mean girls try to rig the votes for prom queen so that Nelly will win. But Chuck over hears them and votes for Blair 150 times so she will win and be happy. Serena and Lily don't see eye-to-eye over Serena's recent run-in with the law and Serena refuses to come out of jail until Lily apologizes. Blair and Nate break up. No Doubt performs in the flashbacks as an 80s band called "Snowed Out."

Gossip Girl sends out a damaging email blast at the Graduation commencement ceremony in which she calls Nate a class whore, Dan, the ultimate insider, Blair a weakling, Chuck a coward and Serena, officially irrelevant. She also exposes the fact that Blair had a one-night-stand with Jack Bass a.k.a Chuck's uncle on New Year's Eve. It makes Serena so angry to have these secrets out for all the world to see, so she tries to unmask the real Gossip Girl. They text Gossip Girl and Jonathan's phone rings. It turns out that he hacked into Gossip Girl's server so he had control over the site but was indeed not Gossip Girl. The identity of Gossip Girl is still a secret. At the after party at Nate's house, Jenny challenges Penelope and the mean girls in an effort to become the next Queen Bee of Constance (but use her title for the good). During the party, Gossip Girl sends another text to everyone, revealing a secret about everyone including Dan's relationship with Rachel, Blair's relationship with Jack Bass, Chuck sleeping with Vanessa, and more, adding that if anyone has a problem about it, they should blame it on Serena because of her obsession with wanting to find out who Gossip Girl is. Serena sends another text message to Gossip Girl telling her to meet with her alone, but Gossip Girl calls everyone else to meet Serena instead, saying that without everyone, Gossip Girl wouldn't exist. One last text from Gossip Girl says that she will keep making posts during college. Georgina Sparks returns and requests to be Blair's roommate at NYU next year, implying that she will cause trouble. Meanwhile, Nate, Dan and Vanessa unknowingly meet Scott, the presumed dead child of Lily and Rufus. Carter Baizen informs Serena that he's located the whereabouts of her and Eric's father. Lily and Rufus finally get engaged. Chuck meets Blair in front of his limo and brings her all of her favorite things from Europe and finally says "I love you too". They kiss making their relationship official.