This article includes a list of the most important episodes of the series to watch, with the most significant events.

 ! This article contains spoilers to those who haven't watched the series yet.
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Season One Edit

  • Pilot (1x01): This episode contains introductions to the main characters and plots for the remainder of season one. This includes Serena van der Woodsen's return to Manhattan, the revelation that Nate Archibald slept with her before she left causing issues with his current relationship with Blair Waldorf, the beginning of Dan Humphrey's relationship with Serena, and Blair's insecurities when it comes to her friendship with Serena.
  • The Wild Brunch (1x02): During this episode, the main issue in Dan and Serena's relationship begins to surface: the difference in their worlds. Also, Dan's sister Jenny Humphrey gains deeper insight into the world of the UES when Blair allows her a bigger role in her group.
  • Poison Ivy (1x03): Blair and Serena's friendship is seemingly repaired after the real reason Serena came home is revealed. Also, Serena's brother Eric van der Woodsen and Jenny strike up a friendship.
  • Bad News Blair (1x04): This episode introduced Carter Baizen, who is a key player in several problems throughout the series. Also, Blair's issues with Serena and her mother begin to resurface and she begins to see Dan as more of an equal.
  • Dare Devil (1x05): Dan and Serena become an official couple, and Blair realizes that she may have met her match when it comes to Jenny. Also, Rufus Humphrey and Lily van der Woodsen grow closer and more is revealed about their relationship.
  • The Handmaiden's Tale (1x06): This episode marks the first appearance of Vanessa Abrams, Dan's childhood best friend. Jenny also defies Blair for the first time, and this begins their power struggle. Nate also admits to Jenny, who is dressed as Serena, that he still has feelings for her.
  • Victor Victrola (1x07): Nate's father Howard Archibald is arrested for fraud and embezzlement, which begins a series of problems with the Archibald family. Also, he and Blair break up and she runs into the arms of his best friend Chuck Bass, and the beginning of the romantic relationship is set in motion.
  • Blair Waldorf Must Pie (1x09): More about the gang's past is brought up when flashbacks of the year prior's Thanksgiving is shown. This includes Dan's long time obsession with Serena, Serena's past of acting wild, and Blair's bulimia and family problems. Also, Rufus, Lily, and Rufus' wife Alison Humphrey's past with each other is revealed to an unknowing Dan, Serena, Jenny, and Eric.
  • School Lies (1x12): Blair and Chuck fight over their affair, and Vanessa captures it all on tape leading to both of them fighting for the evidence. Blair also rejects Nate, who has decided he wants her back, to avoid her sleeping with Chuck being revealed.
  • A Thin Line Between Chuck and Nate (1x13): Dan tells Serena he loves her for the first time. Nate finds out about Blair sleeping with Chuck and cuts both of them off. Blair is also dethroned as queen of Constance.
  • Desperately Seeking Serena (1x15): Serena's old frenemy Georgina Sparks returns to the UES and begins a world of problems for Serena and her friends. Nate and Vanessa begin a romantic relationship.
  • All About My Brother (1x16): Blair and Jenny's power struggle comes to an end, with Blair on top. Also, Eric is revealed to be gay- by Georgina.
  • Woman on the Verge (1x17): The real reason Serena left Manhattan is revealed, and Lily and Rufus reconnect on a sexual level the night before Lily is to marry Bart Bass.
  • Much 'I Do' About Nothing (1x18): Nate and Chuck become friends again after Chuck helps Nate confront his father about leaving the country. Blair and Chuck decide to act on their feelings and spend the summer together in Europe. Lily marries Bart despite still having feelings for Rufus. Nate and Vanessa and Dan and Serena break up.

Season Two Edit

  • Summer Kind of Wonderful (2x01): Serena, Nate, and Chuck have all spent the summer in The Hamptons. Blair returns from Europe with a new boyfriend, Lord Marcus Beaton, in order to make Chuck jealous. Also, it's revealed that Dan spent the summer with different girls to move on from Serena, but neither succeeded at moving on. Nate is having an affair with a married woman, Catherine Beaton, who is Marcus' stepmother.
  • The Dark Night (2x03): Blair and Chuck are revealed to still have feelings for each other. Dan and Serena mutually decide to break up again.
  • The Ex-Files (2x04): Vanessa discovers that Marcus and Catherine are sleeping together, and this begins the rivalry between her and Blair. Dan goes on a date with a new girl, but Serena confesses to still having feelings. Lily tries to be friends with Rufus again but he has no interest.
  • Chuck in Real Life (2x05): Vanessa tries to blackmail Blair but fails, and Blair uses the opportunity to further her games with Chuck. Bart and Lily attempt to convince the world their family is nuclear and perfect but Serena's rebellion causes issues. Also, Nate's living situation is discovered by Dan and Jenny, who try to help.
  • Pret-a-Poor-J (2x08): Jenny begins her downfall rebellion: she quits her job at Waldorf Designs and leaves home. Blair and Chuck decide that a more serious relationship isn't for them yet.
  • Bonfire of the Vanity (2x10) Cyrus Rose is introduced as Eleanor's new boyfriend. While writing an article, Dan discovers Bart burned down a building on purpose to collect insurance money and someone died.
  • It's a Wonderful Lie (2x12): Lily decides to leave Bart to pursue a new relationship with Rufus, but the UES is shaken up when Bart unexpectedly dies in a car accident.
  • O Brother, Where Bart Thou? (2x13): Blair finally tells Chuck she loves him and he doesn't say it back. Cyrus and Eleanor get married after being inspired to live in the moment at Bart's funeral. Dan reveals he still has feelings for Serena despite her current relationship with Aaron Rose. Rufus finds out Lily had his baby years ago but had it adopted.
  • Gone with the Will (2x15): Bart's will is read and Chuck receives the reigns of Bass Industries, much to his Uncle Jack Bass' dismay. Blair again tries to rekindle her relationship with Chuck, but fails and gives up. Jack schemes to take the company from Chuck and succeeds. Lily and Rufus learn that their son died in an accident, and Serena, Eric, and Jenny find out about their half brother.
  • Carrnal Knowledge (2x17): Blair has Rachel Carr fired after she gets expelled from Constance for hazing her, at Dan's expense. Dan and Serena break up once again. Meanwhile, Chuck wakes up in a strange house and discovers a secret society his father was involved in.
  • The Wrath of Con (2x23): Chuck and Nate's friendship once again comes to a head over their feelings for Blair. Georgina arrives back in town and the gang uses her to help take down con artist Poppy Lifton and Serena's boyfriend Gabriel Edwards, who are scamming Lily and her friends for hundreds of thousands of dollars. Chuck lies to Blair and tells her that his feelings for her are just a game because he fears he can't make her happy. Lily has Serena arrested, and Rufus decides to end their relationship after he finds out she was planning to give him money behind his back to help Dan pay for college.
  • The Goodbye Gossip Girl (2x24): The gang graduates from Constance/St. Jude's. Lily and Rufus decide to get engaged. Serena becomes obsessed with discovering the identity of Gossip Girl after she calls her irrelevant, but instead only succeeds in getting a blast sent which includes everyone's secrets. Blair crowns Jenny the new queen of Constance, and her, Dan, and Vanessa are set to attend NYU in the fall. Chuck finally tells Blair he loves her too.

Season Three Edit

  • The Lost Boy (3x03): Georgina sets up Blair and Chuck to fight over the same picture at a Sotheby's auction, but Blair ultimately chooses her relationship and gives it to Chuck. Serena is dating Carter and suspects that he's back to his old bad habits, but figures out it was Blair and Chuck who were setting him up. Vanessa's new boyfriend Scott Rosson reveals that he's Lily and Rufus' son, and that the one who died was his brother Andrew but leaves before telling either of them. Nate's new girlfriend Bree Buckley reveals that she's only hanging around to help her family get Carter for revenge.
  • Rufus Getting Married (3x05): Rufus and Lily decide to move up their wedding to the next day but the wedding is interrupted when Georgina brings Scott back into the city and reveals his secret. Chuck discovers what Carter did to the Buckley's, and gives him the choice to either leave or to tell Serena everything and pay the consequences for what he did. Nate and Bree break up.
  • The Grandfather: Part II (3x08): Nate's cousin Tripp van der Bilt is running for Congress, and wins after a setup to make him look like a hero. Nate and Tripp are led to believe that their grandfather William van der Bilt is behind the scandal, but Nate takes the public bullet. This episode also marks the start of Tripp and Serena's relationship.
  • The Last Days of Disco Stick (3x10): Damien Dalgaard is introduced, and also introduces Jenny to the world of drug dealing. In the aftermath of a threesome, Dan's girlfriend Olivia Burke and Vanessa fight, but Olivia chooses to leave and let Dan and Vanessa figure out their relationship. Nate admits that he loves Serena, but she chooses to be with Tripp after it's revealed the hero set up was orchestrated by his wife Maureen van der Bilt.
  • The Treasure of Serena Madre (3x11): Rufus finds out Lily was lying about where she was during the summer when she was supposedly with her mother CeCe Rhodes. Eleanor reveals her and Cyrus are moving to Paris full time. Serena decides to leave the city with Tripp, after he reveals he's planning to leave Maureen and she finds a letter her father William van der Woodsen wrote her recently that Lily stole. On her way out, Maureen finds the letter.
  • The Debarted (3x12): On the anniversary of Bart's death, Chuck starts to push Blair away. Serena and Tripp get into a car accident and he leaves her hurt and alone. Dan reveals to Vanessa that he has feelings for her. Nate and Serena begin to act on their feelings for each other. Rufus finds out that Lily was with her ex husband, William and isn't sure how far things went with them. Chuck sees a woman whom he suspects may be a piece to the puzzle of some of his father's secrets,

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