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.
Elliot hears Alley break up with Jack on the answering machine. He accidentally erases the message. Finch shares a passionate kiss with Nina and then insults her by telling her she's not his type. Seduction and revenge put Nina on top.
Maya learns of Elliot's criminal past. Nina dates a famous television actor, whose rough-n-tough nomad character melts away once she discovers he lives with his mother. Mamma's not about to share her boy with another woman.
Elliot's brother Donnie who once feigned being mentally challenged so that he could be waited on by his mother returns. He claims to have found a job but is in trouble with some loan sharks but Maya is completely skeptical. When he is supposedly beaten up and winds up in a hospital, she thinks it's a con because all of the hospital staff were at the bistro that she and Elliot met Donnie, thinking they were there to make it appear that they were in bistro. So Maya attacks Donnie.
Maya's high school friend tells her he is responsible for a bad rumor that caused her unpopularity. He's come back to make it up to her. Jack dreams about Kevin killing him. His nightmares continue until he confronts Kevin in an elevator.
When Jack makes Dennis do frivolous errands, Dennis has a meltdown. Jack then sends him to another department where he learns is where Jack sends anyone he gets ticked off with. And Elliot is uncomfortable when he meets Maya's gynecologist who is a good looking guy. He asks her to get another one but she refuses. He later catches the man in a strip club and when he tells Maya she doesn't believe him.