Blair hesitantly returns to school after being dethroned as Queen Bee. Serena struggles to adjust to living with her future stepbrother, Chuck, and receives disturbing packages from an unknown sender. Jenny’s drive to be popular hits a high. Her birthday is coming up, and she feels too ashamed of being middle-class so she steal’s Hazel’s [...]

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. Everyone else also finds out what happened and Blair’s life comes crashing down. Dan struggles [...]

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, because Dan is not ready to [...]

Blair’s father comes home for the holidays with an unexpected guest, his boyfriend Roman. Blair cannot hide her disappointment and makes a plan to get rid of Roman. Jenny and Vanessa help Serena get the best Christmas present ever for Dan, who has a surprise of his own for Serena. When Chuck texts Blair that [...]

Serena had no intention of attending the upcoming Debutante Ball, until her grandmother CeCe announces that she must. Cece does not approve of Dan as Serena’s escort, causing a rift between Serena and Dan. Although they are officially broken up, Nate asks Blair to go to the ball with him. She accepts, but only as [...]

The Humphreys and van der Woodsens share Thanksgiving!!! Dan invites Serena and her family to spend the holiday with his family, creating an uncomfortable situation for Rufus and Lily. The children are unaware of their complicated romantic past. Meanwhile, Blair’s freaks out when she learns that her father isn’t coming home for Thanksgiving. Nate spends [...]

It’s Blair’s 17th Birthday Party! 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 [...]

Serena and Dan finally accept that they are crazy about each other, despite the fact that they come from opposite worlds. Chuck thinks of investing in a club in an attempt to make his father proud of him. Nate confronts his father about the drugs he found in the house, but he denies having a [...]

Masquerade Ball, anyone? 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 [...]

It’s the first official date for Dan and Serena! He tries to impress her 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 [...]