2.01 "Summer Kind of Wonderful" (Season Premiere)

As the summer of the Upper East Siders comes to a close, Blair returns from her summer trip to Europe with a charming new boyfriend, named James, just to make Chuck jealous when she takes him to the Hamptons to spend the last few weeks of the summer with her. However, 'James' is hiding a secret of his own from everyone. Serena, struggling to get over her breakup with Dan, takes a liking to a young lifeguard. Meanwhile, Nate gets involved in a steamy relationship with an older woman, named Catherine whom is married. While Rufus is still on tour with his band, Dan has remained in New York to take a job with a demanding magazine editor, and has gone on a dating spree to get over his breakup with Serena, while Jenny has taken a job at a fashion company working under the cynical, devil-incarnated Laurel, who holds Jenny back for she sees ambitious interns as a threat to her own job.