The first episode of the segundo season is set in the Hamptons and is titled "Summer, Kind of Wonderful," a take from the John Hughes' film "Some Kind of Wonderful." The premiere aired on the CW on September 1st with 3.4 million viewers, an impressive number for The CW network. Season 2 is set to have 24 episodes in all.

It was also announced that The O.C. alum Willa Holland will be reteaming up with Josh Schwartz and will estrella in three o más episodes of Season 2, playing Agnes, a 16-year-old model working for Eleanor Waldorf. Her character is set to create havoc for Jenny Humphrey. John Patrick Amedori has also been cast as Aaron Rose, Serena camioneta, van der Woodsen's new amor interest.

Another character that will be added during the segundo season premiere is Catherine Mason, played por Mädchen Amick. She is an older woman who seduces Nate. She is married and begins having an affair with Nate over the summer, while they are spending time in the Hamptons, on summer vacation. She is the step mother of Blair Waldorf's new amor interest, Marcus (guest estrella Patrick Heusinger). Even though Blair is now with Marcus, a rich English Lord, Chuck regrets losing her over the summer, and tries to win her corazón back. He becomes friends with Marcus in order to get to Blair. And despite Chuck having amor problems, Serena and Dan decide to get back together, however, Serena wants to keep it a secret, eventually, however, everyone finds out via Gossip Girl.

During a city-wide blackout Blair "mistakenly" comes close to having sex with Chuck to fulfill her needs, in which Marcus is depriving her of. Once the lights come back on, Marcus walks in on Blair and Chuck. He proceeds to puñetazo, ponche Chuck, and storm out of the room. Blair quickly follows saying that he is the one she wants, and not Chuck. Marcus accuses her of only wanting his title, however, he wants her as well. Blair then asks him to prove it, and they are seen making out on the stairs of Blair's home.

Meanwhile, during the blackout, Serena and Dan were stuck in an elevator, on their way to Blair's party. There, they are forced to discuss the reasons they broke up in the first place. They decide that they are unable to continue their relationship, and break up, once again. Nate is still secretly involved with Catherine but has a hard time juggling his tryst with her and renewing his relationship with Vanessa. Once Catherine learns of this, she orders Vanessa to steer clear from Nate o she'll go forth with information about Nate's father's whereabouts to the FBI. Vanessa backs off, in order to protect Nate but soon learns that Catherine has been involved with Marcus as well. Instead of going to Nate, she confides in Dan and Blair. Blair composes a plan to blackmail Catherine into paying off Nate's dad's debts but it backfires once Vanessa, out of hurt, reveals to Catherine's husband about her infidelity.

For the first week of their Senior año of school, Dan and Serena avoid each other, until Serena sees Dan talking to the new girl, Amanda (guest estrella Laura-Leigh). Blair and her minions quickly come to the rescue, inviting Amanda to lunch, and leaving Dan without a lunch buddy for the day. Serena feels wrong about trying to keep Amanda and Dan apart, and heads off to find Dan to apologize. Dan, however, blamed Serena for everything, and leaves.

Serena then thinks that it would be a good idea if the three of them went to the club that night. While there, Dan and Amanda begin talking about poetry. Any time Serena tries to add her input, she is proven wrong in what she says and corrected por one of the two. She then decides to go to the bar, and get a drink. There, Blair's friends bring over a guy whom she takes over to the mesa, tabla with her. por this point, Serena is a bit drunk, and she decides she needs yet another drink, and Amanda had gone to the bathroom. Leaving Dan and the new guy alone. Dan gets up and heads to talk to Serena. Serena informs Dan that she can not just turn off loving him, and him having a new girl the first week of school hurt. Dan then says that maybe they'll be better off not being around each other for awhile, and Serena suggests that Dan and Amanda leave. Before Dan and Amanda can leave, though, Blair's friends throw a 'Nairtini' (a liquid that most likely consists of the hair removal product Nair) into Amanda's hair that causes part of it to fall out. While Serena is not at fault, Dan blames Serena for this and storms out, after sparking her jealous and mean side. It is later revealed that this whole scheme was plotted por Chuck, having hired Amanda and setting up the fake relationship to once again return Serena to her reign as queen of the school. This sudden shift in Serena's behavior is already evident and brings Blair much chagrin, but delights Chuck in his hopes to knock Blair off of her pedestal once again.

With Fashion week on the horizon, Blair knows she can reclaim her trono por helping her minions get in to Eleanor's show. Soon Blair discovers that not only is Serena on the radar with her new socialite friend amapola Lifton (guest estrella Tamara Feldman), but Jenny is the shining estrella at Eleanor's studio. Jenny has not only changed the seating chart that Blair designed, but she's garnered a lot of attention for her work. Blair soon decides to sabotage the mostrar por sending the modelos home, (which Jenny saves por having the socialite friends of amapola and Serena model for the show) and even sends Serena down the pista, pista de aterrizaje in a dress that Jenny made. As expected, Eleanor is furious to find Jenny's dress on the runway, but Blair soon realizes Jenny is not the enemy and steps up for her. Eleanor receives rave reviews for Jenny's dress. Serena and Blair have an altercation that can best be described as a "you hold me back, I want to be all that I am," to which Blair is not amused. Tensions are high when Blair sees photographers taking fotos of amapola and Serena while they are leaving the show. A subplot of this episode finds Dan attempting to experience life in Chuck's shoes, which leads him to discover a dark secret about Chuck and Bart's relationship. Lily also unearths that Bart has gone to great lengths to assure nothing from her past can destroy their family, which includes a file on Lily's life before her turn as an Upper East Side mother. Rufus and Jenny are also on the outs, due to Jenny's refusal to attend school. She wants to focus on her talent as a designer, much to Rufus' chagrin.

Jenny's disagreement with Rufus finally comes to an end when he agrees to spend one día with her at Eleanor's studio before making the final call as to whether she must return to school on Monday. A supposedly accidental run-in with Lily causes the single father to realize that he should let his daughter follow her dreams, because even though he wasn't able to follow his, they are in reach right now for Jenny. With the help of Vanessa, she decides to be home-schooled. Meanwhile, Blair, Serena, Dan, Nate and Chuck visit Yale universidad to give them a taste of college life there. Although Serena was originally going to visit Brown University, she ditches this plan in order to get even with Blair por impressing the Dean of Yale so much that he invites her to an intimate gathering at his house. In a rage, Blair manipulates her way into the dinner, and the night ends in a girl-on-girl catfight between the two best friends. Chuck, Dan and Nate all get themselves into trouble with Dan realizing that none of his recommendation letters were ever submitted, Nate being head-hunted because of his father's actions, and Chuck being kidnapped por a group of Skull and bones members who want to use him to get even with the Archibald family.