S5, E5: In the midst of celebrating Yom Kippur with family and friends, Blair and Louis (recurring guest star HUGO BECKER) find themselves in a power struggle with Louis' family. Serena's boss (recurring guest star MICHAEL MICHELE) puts Serena in the awkward position of choosing between her new job and her relationship with Dan. Meanwhile, Diana (recurring guest star ELIZABETH HURLEY) prepares to debut the New York Spectator, but an unfortunate last-minute surprise delays the launch and Diana expects Nate to do whatever it takes to save the day.