As the summer is drawing to a close, Blair and Chuck are madly in love and adjusting to their new "in a relationship" status, breaking all traditional rules of dating as would be expected. Meanwhile, Serena returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen. Nate returns from his travels with a mysterious brunette, Bree Buckley (guest star Joanna Garcia) in town. With Lily away in California visiting her mother, Rufus, Dan, and Jenny spent the summer in the Hamptons, adjusting to the van der Woodsen's glamorous lifestyle surprisingly faster than any of them expected. Also, Vanessa introduces her new boyfriend, Scott, to Dan and Rufus.