Olivia says something she regrets during her appearance on Jimmy Fallon's talk show and tries to keep Dan from finding out. With election day around the corner, Nate suspects his grandfather will stop at nothing to get his cousin Trip (guest star Aaron Tveit) elected to congress. In the midst of another feud with Serena, Blair befriends a new "it" girl and takes her to an election night party at Chuck's hotel, hoping to make Serena jealous. Meanwhile, Vanessa becomes upset with Nate because of his schemes during the election.