A photographer coerces Elliot into hiring him as his assistant. Elliot doesn't want to be under his thumb but doesn't know what to do. An astronaut comes to for an interview but Nina thinks the whole going into space is a hoax.
Maya and Elliot are going out on a date. But Cindy, Maya's former secretary who's now a media buyer wants to get space in the magazine. So she goes out with Maya and Elliot and they all get drunk. Elliot wakes up to find himself in bed with Cindy. When Maya learns of this, she's shocked and wants nothing to do with Elliot. Finch trying to get over the end of his marriage to a model thinks he should hook up with another. While Jack tries to get him to take up a hobby.
When Elliot brings his new girlfriend to the office, Maya's expecting another dumb blonde. But when he reveals her to be a doctor, she's amazed. Eventually Maya lets it slip that Elliot lied to her about himself that she breaks up with him. Elliot is upset that Maya would do that to him that she tries to fix things. And when she goes on about Elliot, she wonders if she has feelings for him.
Nina's former agent whom she cast aside when she made it big calls her and she makes an unusual request. When Nina has to do something she passes her to Finch who hits it off with her. Maya thinks her new boyfriend has unusual fetish.
Dennis runs into Adrianne and upon learning that she thinks of him decides to try and get back together with her. Jack is selling cookies that his daughter is selling at her school and is "asking" his employees to buy. Elliot who likes the cookies wants to buy. But Maya who doesn't like what her father is doing; "tells" Elliot not to and if he does she'll reward him in the bedroom. When Jack hears of this he says Elliot is under Maya's thumb.
The unexpected arrival of his old figure skating partner has Finch worried. Following an accident on the ice nearly twenty years ago that ended her skating career, Nicole stopped speaking to Finch. And while he was upset over losing a partner, the hurt.