Original Air Date: 19 May 2008
Blair takes matters into her own hands to help Serena deal with the manipulative and evil Georgina Sparks who threatens to expose Serena’s secret. Lily, while keeping Rufus in her mind, prepares for her wedding with Bart Bass that is designed to be the Upper East Side’s social event of the year. Serena finally tells Dan the whole truth about her past and about Georgnia and they try to work things out. But Dan is guilt-ridden after having cheated on Serena with Georgina and wonders if it is already too late. An unexpected guest shows up at Lily and Bart’s wedding. Also Blair manipulates matters so that Georgina goes “somewhere where she can do no harm”. As the end of the school year approaches, Blair plans to go somewhere with Chuck.

Original Air Date: 12 May 2008
Serena reveals to Blair true reason why she left Manhattan: to avoid being implicated in an accidental drug overdose of a school friend in which Georgina was also present. Serena goes back into her old habits of drinking and drugs. Blair, Nate, and Chuck are forced to team up to try to help Serena. Unfortunately, Serena is too ashamed to share the truth with Dan about her mistake, therefore he assumes the worse about his girlfriend. Blair also discovers from Vanessa that Georgina, under her alias ‘Sara’, is still hounding them pretending to be their friends. Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stones sponsored concert. But Lily is the last person on Earth he expects to see at the performance, especially since her wedding rehearsal dinner is on the same night.

Original Air Date: 5 May 2008
Georgina tells Serena that she can reveal a deep dark secret from Serena’s past, but no one is prepared for what Georgina does next. Meanwhile, Blair and Jenny’s power struggle continues when each of them start spreading false and scandalous rumors about each other on Gossip Girl’s blog. Dan sees Jenny’s new beau Asher cheating on her and tells her, but Jenny refuses to believe Dan. Rufus goes to Lily for advice on how to handle Jenny’s new rebellious behavior. Serena tries to confront Georgina, but she skips town before Serena has a chance. After this, Serena tells Lily and everyone she and Georgina are not friends after discovering that Georgina has been lying to everyone, claiming that she and Serena are still friends.

Original Air Date: 28 April 2008
Serena’s world becomes chaos when a former friend-turned-enemy, the evil and sociopath Georgina Sparks, returns to town and transfers to her school. Dan sees Serena preoccupied and he assumes that it has something to do with the nasty Chuck, who’s looking forward to making her life a living-hell as her soon-to-be step-brother. Nate connects with the last person he expected, Vanessa over his failed relationship with Blair. Serena goes out with Georgina for a night on the town to try to patch things up between them, but things get so bad that Serena thinks someone spiked her drink. Meanwhile, Hazel and Penelope try to recruit newcomer Nelly Yuki to be part of their gossip club, but it is not easy. Blair supervises the whole operation and hatches a plan to sabotage Nelly. When Nelly breaks down after being reminded of her recent break-up with her boyfriend, the ladies find their way in and Nelly comes to the Waldorf penthouse where Blair tries to repair the damage. Elsewhere, Jenny develops a crush on 16-year-old dog-walker, Asher Hornsby, who might be her ticket to permanent popularity.

Original Air Date: 21 April 2008
Spring Break is over, and so are all of Blair’s days of hiding away. Finally, after three weeks, she comes back to school, with an unpleasant welcome by Jenny and the “in” crowd, who throw ice cream in her hair. Serena believes that being mean was got Blair kicked out of the “in” crowd in the first place and dethroned “Queen Bee.” When Jenny asks Blair to meet her at Butter along with all of Blair’s former friends, Serena finds it the perfect opportunity for Blair to show just how nice she is. But the situation goes from nice to sour when Jenny and her friends purposely don’t show up, leaving Blair all alone. Meanwhile, Jenny needs something to wear for her 15th birthday party, and eventually ends up stealing one of her friend’s mother’s dresses in exchange for a $1,200 dress in an exchange shop. But when Jenny tries to get it back, she learns the red dress is over $8,000. Once again, Jenny steals the red dress, throwing her coat over the dress. She comes home to a 15th birthday party created by none other than Blair, who talked to Jenny’s dad, and made the birthday party as lame as possible. While Jenny’s dad doesn’t realize how lame the party is, Jenny’s friends do, and are about to leave when they find Jenny wearing the red dress. They ditch the birthday party and meet Blair at Butter. Thinking quickly, Jenny sneaks out and has Nate accompany her to Butter. Jenny’s friends are pleased that Nate, who they are attracted to, is hanging out with them, and “forget” the incident with the dress, leaving Blair friendless once again. Also, Serena adjusts to her new living conditions with Chuck, but when she receives inappropriate gifts, she believes Chuck sent them. But, at the very end of the episode, she learns who really sent them, and it wasn’t Chuck.