Ep 18. Miss Pretty

When Maya wants an interview with the magazine's popular new advice columnist, she asks Finch to arrange it. Even after Finch reveals that Miss Pretty is actually a man, Maya still wants the interview. So, because he doesn't want anyone to know that he's actually the columnist, Finch enlists his friend, small time con man Kurt Bell, to help out. Meanwhile, as a mistake forces Nina to have lunch with an acquaintance she doesn't really like, Elliott misidentifies Kevin Tanaka, one of the magazine's biggest advertisers, for a Chinese food delivery boy. Intrigued by Kurt and impressed with his sensitivity, Maya agrees to a dinner date. But when Finch worries about Maya being used, he warns Kurt to steer clear. Yet, despite Finch';s efforts, Maya accepts Kurt's invitation for a weekend in the country. Meanwhile, as Nina cannot avoid spending time with Carol, Jack gets Elliott to apologize, only to mistake an Asian employee at the magazine for Kevin. Realizing that Kurt just wants to get Maya into bed, Finch breaks the news that he's Miss Pretty. Reluctant to believe it, Maya puts each man to the test with a question and discovers that Finch is right. Finally, upon arriving at the office for his apology, Kevin misinterprets Elliott's innocent gesture as a racial slur. And despite being made to feel sorry for Carol, Nina insists that their renewed friendship must come to an end.