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