In the midst of celebrating Yom Kippur with family and friends, Blair (Leighton Meester) and Louis (guest star Hugo Becker) find themselves in a power struggle with Louis' family. Serena's (Blake Lively) boss (guest star Michael Michele) puts Serena in the awkward position of choosing between her new job and her relationship with Dan (Penn Badgley). Diana (Hurley) prepares to debut the New York Spectator, but an unfortunate last-minute surprise delays the launch and Diana expects Nate (Chace Crawford) to do whatever it takes to save the day.