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.
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