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Video: Reversals of Fortune

As the summer draws to a close, Blair (series star Leighton Meester) and Chuck (series star Ed Westwick) are madly in love and adjusting to their new "in a relationship" status, though breaking all traditional rules of dating, as would be expected. Serena (series star Blake Lively) returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen (recurring guest star Sebastian Stan - Kings). Nate (series star Chace Crawford) returns from his travels with a mysterious brunette, Bree Buckley (recurring guest star JoAnna Garcia - Privileged, Reba) in tow. Rufus (series star Matthew Settle), Dan (series star Penn Badgley) and Jenny (series star Taylor Momsen) spent the summer in the Hamptons, adjusting to the van der Woodsen's glamorous lifestyle surprisingly faster than any of them expected. The series also stars Jessica Szohr as Vanessa and Kelly Rutherford as Lily van der Woodsen Bass.

Video: Valley Girls

In a special flashback to the 1980s, before she became Lily van der Woodsen, 17-year-old Lily Rhodes (guest star Brittany Snow - "American Dreams," "Hairpray") is kicked out of boarding school and runs away to Los Angeles to reconnect with her parents, Rick (guest star Andrew McCarthy - "Lipstick Jungle," "Pretty in Pink") and CeCe (guest star CYNTHIA WATROS - "Lost"), and her older sister, Carol (guest star Krysten Ritter - "Confessions of a Shopaholic"). Plus, No Doubt performs as an eighties band called Snowed Out. Back in present day New York City, Blair and Nate attend the prom together, but the evening doesn't turn out exactly as planned -- something Chuck may have a little to do with. And Serena and Lily don't see eye to eye over Serena's recent run-in with the law. Recurring guest star Michelle Trachtenberg appears as Georgina.

Gossip Girl Spin-Off Crosses With The O.C. ???

In just a couple weeks more, Gossip Girl fans can go back in time to witness Lily van der Woodsen during her younger years.  As reported previously, the May 11 episode of Gossip Girl will take the form of a prequel, laying the groundwork for a spin-off that could start as soon as the fall.  So far, we already know that Brittany Snow (American Dreams, Nip/Tuck) will be playing the younger Lily, while Krysten Ritter (Veronica Mars, Breaking Bad, ‘Til Death) has been cast for the part of Lily’s troubled older sister, Carol.  Moreover, Jericho’s Shilo Fernandez has also signed on to play Owen, a brooding valley punk.

But that’s not all.  According to Entertainment Weekly, executive producer Josh Schwartz and co-creator Stephanie Savage are contemplating on the idea that Lily may have crossed paths with characters from their previous hit, The O.C., which ended its run on FOX in 2007.

In line with that, Schwartz and Savage are toying with the notion of having Lily interact with earlier versions of some of The O.C.’s most notable characters including Kirsten Nichol, Jimmy Cooper and possibly a young Julie Cooper, who was previously played by Melinda Clarke.

The O.C. became an instant teen favorite when it premiered on the FOX Network in August 2003.  The show popularized its setting, Orange County, and led to shows like MTV’s reality series Laguna Beach: The Real Orange County and the Bravo documentary series The Real Housewives of Orange County.

While there might be some familiar faces on the spin-off, Schwartz reveals that there won’t be any from Gossip Girl so fans of Lily and Rufus shouldn’t expect the rockstar dad to show up.

“It’s not the story of how Lily met Rufus,” executive producer Josh Schwartz explained.