Serena van der Woodsen unexpectedly returns to the Upper East Side, Manhattan from her mysterious stay at a boarding school in Connecticut. She is initially unwelcome by her best friend Blair Waldorf, who was perplexed by the lack of contact during Serena's absence, and has assumed the position as queen bee of the Constance Billard junior class. At first the two awkwardly struggle for the top, however after discovering that her longtime boyfriend Nate Archibald had slept with Serena (just before they have sex, where Blair would have lost her virginity) and caused her departure, Blair is unwilling to continue their friendship. Serena meets Dan Humphrey, a new St. Jude scholarship student and outsider to Upper East Side life, and begins a relationship with him. At the same time Dan's father, Rufus, and Serena's mother, Lily, rekindle their past relationship. It is revealed that Dan has dreamt of dating Serena for some time and even wrote a story that would go on to be published in the NYT. After Blair continues to ruin Serena's reputation Serena fights back, however it all comes to an end when, whilst at an Ivy School Mixer Blair informs everyone that Serena is battling a drug addiction after Chuck sees her attending the Ostroff centre. Serena's brother, Eric van der Woodsen informs blair that he had attempted suicide and was receiving treatment, which explains why she came home. After a tearful explanation of how much she needed Serena and how Serena had abandoned her, Serena and Blair mend their friendship.
While Dan is adamant about keeping a distance from the upper east side, his sister Jenny desperately attempts to fit in, performing menial tasks in order to be a part of high society. This involves a game of truth or dare which could have potentially ending in Jenny's arrest, acting as a "Handmaiden" and slave to Blair and a hazing from her friends. Despite Blair's attempts to rectify and mend her relationship with Nate, it slowly begins to fail due to Nate's personal problems with his father, which include his father's drug addiction and money problems and the fact that he still loves Serena. When Nate gets his father arrested, Blair informs him that she doesnt need him, but his family does and leaves him. Distraught Blair performs a strip tease at his club, Victor Victrola which ends with Blair losing her virginity to Chuck Bass, Nate's best friend, in the back of his limo. Chuck eventually develops feelings for Blair, admitting to them on her birthday while she waits for Nate to come (no one knows they are broken up), however Gossip Girl sends out a picture of Nate blowing off Blair's party with Jenny causing Blair to admit to everyone that they aren't together and she once again hooks up with Chuck, something Serena witnesses. After their fling Blair tries to mend things with Nate, however Chuck prevents her from reviving her relationship with Nate by threatening to tell him of their shared intimacy. Throughout the year, Serena and Dan's relationship is continually tested by the elite class and the return of his best friend Vanessa Abrams who Dan confessed his love for the year earlier. Yet, despite such problematic situations, their relationship grows stronger and Serena moves past her insecurities over Vanessa knowing Dan so well and he moves past his own over their different worlds.
Blair's relationship with Nate is going well, after she is sure he wont tell Nate anything. However, Gossip Girl sends out pictures of Serena buying a pregnancy test and Dan professes his love for her. She informs him that she isnt pregnant and later. during a date, Serena tells Dan that Blair slept with Chuck and Nate within the same week. Jenny overhears this and her desire to become a part of the upper east side coupled with her hatred of Blair's belittlement compels her to confirm to Nate of Blair's transgressions after he doubts the verity of the Gossip Girl blast Chuck sends out informing everyone so.
Nate then publicly confronts Chuck while the entire school watches, destroying Blair's reputation as being perfect and 'dethroning' her as the queen bee. Blair has a breakdown and sees that she has lost everyone compelling her to jump a private plane to France to spend a semester with her father and his gay lover. Serena intercepts her before she leaves and promises to help her through the scandal, telling her not to make the same mistake she did. In Blair's absence, Jenny begins to ascend the ranks at Constance Billard and terrorizes Blair when school comes back after Spring Break. Blair however, seeks revenge and later defaces Jenny by organizing a party at her loft which reveals that she stole Hazel, one of Blair's minions, mother's Valentino dress to sell to a pawn broker for a Dolce. The girls shun Jenny and go back to Blair before Jenny make a return by asking Nate, a now close friend, to talk to Penelope, who has had a crush on him for a while.
Meanwhile Lily and Chuck's mogul father, Bart Bass, get engaged after Serena tells her mother that she would prefer to have Chuck as a step-brother over Dan and saying that she loves him. All is well for a while until Serena starts receiving racy gifts that she first links to Chuck. However, she soon discovers that they are from Georgina Sparks who Serena partied with a year earlier. Georgina returns and Serena claims she isnt interested in partying with her anymore. Georgina however has befriended Dan, under the alias of Sarah, and continues to be a fixture in Serena's life, threatening to tell Dan about the night before Serena left. Georgina invites herself to dinner and outs Serena;s little brother, Erik, of being a homosexual with Jenny's boyfriend. Serena is disgusted that she would do this and says that she never wants to see her again. Georgina still doesnt leave and Serena and Dan's relationship begins to suffer and Lily finds a USB which has a video of Serena and Georgina and a boy named Pete Fairman. The video shows Serena refusing to have sex with him and he does a line of cocaine which results in his death. This teamed with her sex with Nate is revealed to be the reason behind why she left. Serena tells Blair all of this, claiming that she killed Pete, holding herself wrongfully responsible for his death. Chuck, Blair and Nate decide to take Georgina down.
Unfortunately Georgina has seduced Dan and Serena walks into his loft and believes to find them in the aftermath of having sex, which actually did not occur. The closing of junior year is happens at the Bass wedding where Lily walks down the aisle, despite having sex with Rufus the night before and Dan, who is unable to cope with the lies and class differences that separate him from Serena, breaks up at the Bass wedding. Blair and Chuck rectify their broken relationship at the Bass wedding but later fails because he is afraid of truly committing himself to her, bailing on their planned trip to Europe.
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