(Chuck and Blair return from their long Monaco honeymoon)

Serena: "B!" (Stepping off the elevator into The Empire apartment)

Blair: "S!"

(The friends share a long hug)

Serena: "How was Monaco Mrs. Bass?"

Blair: "Amazing. Chuck and I are fabulous."

Serena: "B, you are glowing, truly."

Blair: "While I'm glad you noticed because Chuck and I discovered something while we were in Monaco…I'm pregnant."

Serena: "Oh My God, Blair! (hugging her) congratulations!"

Blair: "I'm already designing a maternity line because I refuse to not look fabulous while pregnant."

Serena: "I have news too, although it can't compare to that…Nate and I are back together."

Blair: "Oh S! That's wonderful, you two are legendary."

The gang of the Upper East Side all begin to find their way. Dan continues to write books based off of his Gossip Girl experience, even writing a series called the Inside. Vanessa makes successful documentaries about life in and outside of New York. Dan and Vanessa stay committed to each other despite the distance of Vanessa's job. The two eventually marry in a small Brooklyn ceremony.

Serena and Nate continue to support each other in their endeavors and travel the world together. Serena becomes the ambassador of numerous charities, while Nate takes the Spectator global. Serena proposes to Nate on New Year's Eve 2015 on a yacht in the Caribbean.

Chuck and Blair continue to dominate Manhattan together. Blair's fashion empire grows from clothes to handbags, make-up, and other accessories. While Chuck continues to run The Empire, his night clubs, and even opening the Chuck Bass Hotel. Blair gives birth to a son named Henry.

Jenny continues to rule the teen fashion world until she discovers her hidden talent for music with the help of 19 year old Easy Walsh. The two meet at a Lincoln Hawk reunion concert and instantly connect. Easy is the lead guitarist of a band but is missing a lead singer. After accidently over hearing Jenny sing, Easy convinces her to join the band. They became The Reckless, releasing a lead single called Zombie. A song Jenny wrote about her rebellion of the Upper East Side. Jenny and Easy become a couple.

Eric attends Saint Martin's College of Arts and Design. After accidentally running into Jonathan on campus, the two reconnect and resume their relationship. Eric continues to volunteer his time and experience through email to teens at the Ostroff Center throughout the school year.

Rufus and Lily's marriage stands the test of time among the Upper East Side socialites, as Lily continues to be a successful socialite and Rufus continues to manage and produce rock bands, including Jenny's band The Reckless.