"It girl" Serena van der Woodsen has returned to Manhattan after a mysterious and self-imposed exile to boarding school. Serena's best friend, Blair Waldorf, has conflicted feelings about her friend's return since she has enjoyed being the Queen Bee during Serena's absence and might not be ready to relinquish her new position on the social ladder, not to mention the fact that she has always suspected there may be unspoken feelings between Serena and her longtime boyfriend, Nate.

It's the day right after the Kiss on the Lips party and Serena receives a cold reception from her former best friend Blair. Blair reveals that she knows that Serena and Nate slept together, before Serena mysteriously went to boarding school. Then Serena decides to take Dan to Chuck's fundraiser brunch at The Palace. Meanwhile little Jenny asks Blair for advice, and Blair realizes that she maybe gains something by allowing Jenny into her inner circle.

It's Ivy week for the Upper East Side teens of Constance Billiard and St. Jude's and the visiting representatives' arrival brings more than just college applications. Cut-throat rivalry is at its sharpest this week as the students compete for prestigious positions. Blair discovers a shocking but juicy secret about Serena and plots to drop the bomb at the best possible moment. Dan is sure that landing the coveted usher position with the Dartmouth rep will either make or break his future at the school. Unfortunately, it's Nate who nabs the position, despite total disinterest in the school. Meanwhile, Jenny gets closer to Serena's younger brother Eric and Rufus asks Lily for a favor.

Blair gets excited when her mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair's happiness turns quickly into feelings of betrayal and jealousy when Serena takes her spotlight and Blair finds herself back in Serena's shadow. Meanwhile, Serena and Dan remember once again that they come from two very different worlds. Also, Nate and Chuck do a boys weekend to blow off steam after Ivy Week ends.

It's their first official date and Dan tries to impress Serena with an elaborate plan for the date, but fails to understand that Serena is happier with beer than champagne. That same night Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high stakes game of "Truth or Dare". Meanwhile, Lily finds out that Erik is missing from the treatment center, and she finds herself seeking help from her ex-boyfriend, Rufus.

Dan finds himself between two girls when his childhood friend, Vanessa, returns to N.Y. and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At the masked ball, Blair sends Nate on a scavenger hunt, but Nate is distracted by his feelings for Serena. Although Blair said that outsiders were not welcome to the party, a disguised Jenny and Dan sneak into the ball. Finally, Lily asks Rufus to accompany her to an Eleanor Waldorf event only to make Bart Bass jealous.

Serena and Dan finally accept that they are crazy about each other, despite that they come from polar opposite worlds. Chuck thinks of investing in a club trying to make his father Bart Bass proud of him. Nate confronts his father, about the drugs he found in his house but he denies having a problem. Jenny discovers a secret that her parents have been keeping from her. Finally, Blair is devastated by Nate's actions when Jenny reveals that Nate kissed her by accident thinking she was Serena.

Blair is feeling heartbroken and guilty by the current state of her relationship with Nate and her recent indiscretion. But she manages to put on a happy face for her 17th birthday party and attempts to hide her feelings from her friends. Hoping that Serena and Vanessa can bond, Dan takes Vanessa to Blair's birthday party. Jenny brings her mother home as a surprise, but Rufus isn't ready to forgive and forget. Finally, Nate's parents ask him to make a huge sacrifice to save his father's business.

Serena's grandmother announces that Serena has to go to Debutante Ball. However, Dan is not what CeCe wants as an escort for Serena, and she makes her opinion heard loud and clear, causing a rift between Serena and Dan. Although they are officially broken up, Nate asks Blair to go to the ball with him. A jealous Nate begins to suspect that Blair is seeing someone else. Jenny finds herself having to make the decision of either attending her mother's art opening or following her dreams to the Debutante Ball, even though her parents don't want her to go.

Serena, Blair, Nate, Chuck and their class break into the school swimming pool for a night of fun, but when someone nearly dies, the school threatens to expel the person responsible for the break-in. Everyone agrees to not say anything, but this creates major problems between Serena and Dan. Vanessa, while working on a documentary project about private schools, accidentally captures Blair and Chuck discussing their affair. Lily tries to tell Rufus how she really feels about him.

Gossip Girl reports that Serena van der Woodsen was seen buying pregnancy tests. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip. Nate finds out about Blair and Chuck's affair. And when everyone else finds out what happened Blair's life comes crashing down. Meanwhile, Dan struggles to tell Serena those three special words.

Having been recently dethroned as Queen Bee, Blair returns to school with the support of Serena to find she is still on the outs with her old friends. Dan visits his mother over spring break, and when he returns, Jenny is on the verge of becoming a full-fledged member of the A-List crowd. Jenny must go to dangerous and even illegal lengths to fit in. Serena struggles to adjust to living with Chuck, and receives disturbing packages from an unknown sender.

Serena's world descends into chaos when a former friend, the evil Georgina Sparks returns to town. Nate connects with the last person he expected, Vanessa. Blair hatches a plan to sabotage her biggest rival, Nelly Yuki. Meanwhile Serena goes out with Georgina, but things get so bad that Serena thinks someone spiked her non-alcoholic drink. Jenny develops a crush on a dog-walker, Asher Hornsby, who might be her ticket to permanent popularity.

Georgina informs Serena that she can reveal a deep dark secret from Serena's past, but no one is prepared for what Georgina does next. Blair and Jenny's power struggle continues when each of them start spreading scandalous rumors about each other on Gossip Girl. Dan sees Jenny's new beau, Asher, cheating on her, but Jenny won't listen to him. Rufus goes to Lily for advice on how to handle Jenny's new behavior. Serena tries to confront Georgina, but she leaves before Serena has a chance. After this, Serena says that she and Georgina are not friends.

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.

Blair and her minions decide to befriend the new girl, Amanda, in order to sabotage her possible new relationship with 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 protege Jenny, has given Serena and her new socialite friend, Poppy Lifton, 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.

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. 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 isn't ready to play by their rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

Blair sets out on a mission to break up her mother and Cyrus Rose, her new man. Jenny moves in with Agnes as the two continue with their plans for their own fashion line. As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for New York Magazine.

At the Snowflake dance, Blair and Chuck discover their lookalikes hooking up. Aaron's ex Lexi flirts with Dan, causing trouble with Serena. Nate, Jenny and Vanessa get into a messy love triangle that involves a stolen letter and a revealing dress. Bart Bass suffers a car accident on his way to the ball.

Because Chuck is MIA since his father's funeral, his Uncle Jack arrives on the Upper East Side to find and help him. Trying to forget her last conversation with Chuck, Blair focuses 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.

Chuck, Jack and Lily come together for the reading of the will which reveals what will come of the Bass empire. Rufus and Lily's relationship is put on hold as Rufus searches for the child he never knew he had. Meanwhile, Dan does some digging of his own and uncovers Rufus and Lily's secret, putting him in an awkward position.

The students are stressed out as they find out who was accepted and who didn't make the cut for early admission to Yale. Meanwhile, Serena bonds with Rachel, her Shakespeare teacher, who is unaware of what Blair has in store for her following receiving her first B; Chuck finds an unlikely ally in his feud with Jack; and Nate and Vanessa have a romantic evening together.

Blair comes up with a devious plan to take down her new teacher, Rachel. Chuck has no recollection of what happened to him when he wakes up in a hotel. Nate and Vanessa try to help Chuck fill in the missing pieces of his night. Meanwhile Dan and Serena try to keep their relationship together as Rufus and Lily grow even closer.

The Constance Billard and St. Jude seniors have the production of "The Age of Innocence". Serena has a crush on the play's director, Julian, and enlists Vanessa's knowledge of theater to help her get the guy's attention. Blair receives bad news about her future that leads her on a witch hunt for the person responsible. 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. Chuck find help on an unlikely friend, Carter Baizen.

Serena throws Jenny a sixteenth birthday party, but things spin out of control when Poppy Lifton turns the party into the social event of the season. Vanessa agrees to help Chuck in a plan concerning Blair and Nate. Meanwhile, Rufus searches for a way to cover Dan's tuition when he learns he will not receive financial aid to go to Yale.

In a flashback to the 80s, 17-year-old Lily Rhodes gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick and Cece, and sister, Carol. Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out exactly as planned and Chuck and Serena have a little something to do with that. Serena and Lily don't see eye-to-eye over Serena's recent run-in with the law.

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. The Mean Girls challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year. Lily and Rufus struggle to repair their relationship after Lily’s betrayal. As for the cliffhangers, Blair and Chuck finally… and Serena is shocked by… and Georgina decides to… and Dan, Nate, and Vanessa unknowingly…. Jenny and Eric do something they might end up regretting.

Charlie is finally starting to feel less like a fish-out-of-water with Serena and her friends, but complications present themselves when Charlie is invited to attend the Constance Billard alumni fundraiser. On the road to "happily ever after" Blair finds herself torn between the men in her life. Jack Bass return to the Upper East Side sets off a chain of events that could end up destroying Chuck and those closest to him.

The episode continues from the early events of the Constance Alumni event. Georgina Sparks turns up at the event looking for trouble. Serena and Vanessa reluctantly join forces to find Dan and Charlie, who does not take Dan's rejection of her well. Blair must make a choice between the men in her life when her life is in danger by Russell.