Season 3: Episode 49: Miss Pretty
Maya decides that since the new Miss Pretty column is so good, she will do a column on Miss Pretty. Finch then informs her that the new Miss Pretty is actually a man, but Maya thinks that will make the article even better, and insists on meeting him. Meanwhile, Nina finds herself roped into an unwanted friendship with a woman she can't stand, and Elliott and Jack find themselves in hot water when they accidentally insult an Asian-American executive from an important advertiser.