Nate dons his best suit for his first day as an intern at Diana's newspaper. His new business duds aren't lost on his boss, who immediately fires her staff so she can get it on with Nate in the office. In order to placate Nate, she throws him an assignment to interview a congressman and his wife, only to trick him into exposing the husband's infidelities. Diana reveals she's actually on a quest to become the new Gossip Girl, and when Nate stupidly suggests that a better tactic would be to infiltrate the phones people have checked in at a party, Diana jumps at the idea. Nate hesitates, but she quickly plays on his weaknesses, telling him he can always get a job through his mom if he's not up for her style of reporting. Ivy/Charlie's phone is among the stash the pair snoops in, which means Nate could be on to Charlie's true identity soon.