The privileged prep school teens on Manhattan's Upper East Side first learn that Serena van der Woodsen (Blake Lively, "The Sisterhood of...

The privileged prep school teens on Manhattan's Upper East Side first learn that Serena van der Woodsen (Blake Lively, "The Sisterhood of...

The privileged prep school teens on Manhattan's Upper East Side first learn that Serena van der Woodsen (Blake Lively, "The Sisterhood of...

In the wake of the scandalous Kiss on the Lips party, Serena receives an ice-cold reception from her best friend, Blair, who reveals that...

In the wake of the scandalous Kiss on the Lips party, Serena receives an ice-cold reception from her best friend, Blair, who reveals that...

In the wake of the scandalous Kiss on the Lips party, Serena receives an ice-cold reception from her best friend, Blair, who reveals that...

Ivy week equals drama as the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from the Ivy...

Ivy week equals drama as the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from the Ivy...

As the teens prepare for Ivy League college representatives to visit their campuses, Blair uncovers a secret about Serena that she has not...

Blair is thrilled when her mother chooses her to be the new face of her clothing line. However, Blair's happiness soon turns to feelings...

Blair is thrilled when her mother chooses her to be the new face of her clothing line. However, Blair's happiness soon turns to feelings...

Blair is estatic when her mother chooses her to be the face of her clothing line. However, her joy is short-lived when Serena once again...

Dan makes elaborate plans to impress Serena on their first official date. On the same night, Jenny is invited to the infamous Blair...

Dan makes elaborate plans to impress Serena on their first official date. On the same night, Jenny is invited to the infamous Blair...

Dan goes to extensive lengths to make his first date with Serena perfect. That night, Jenny is invited to Blair's sleepover where a...

Dan is torn between two girls when his childhood friend, Vanessa (recurring guest star Jessica Szohr), returns home and declares her...

Dan is torn between two girls when his childhood friend, Vanessa (recurring guest star Jessica Szohr), returns home and declares her...

Dan's childhood pal Vanessa returns to town and tells him she wants to be more than friends. Meanwhile, Blair does her best to keep party...

After surviving their relationship's on-again/off-again genesis, Serena and Dan finally acknowledge that they are crazy about each other,...

After surviving their relationship's on-again/off-again genesis, Serena and Dan finally acknowledge that they are crazy about each other,...

Though being on again, off again for the past few weeks, Dan and Serena finally admit to one another that they are crazy about each other,...

Devastated by the state of her relationship with Nate and still dealing with the guilt from a recent indiscretion, Blair puts on a happy...

Devastated by the state of her relationship with Nate and still dealing with the guilt from a recent indiscretion, Blair puts on a happy...

Blair attempts to hide her strained relationship with Nate during her 17th-birthday party. Meanwhile, Dan invites Vanessa to the party in...

When Dan finds out that Serena and her family are celebrating Thanksgiving alone, he naïvely invites them to spend the holiday with his...