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.
When Finch's newly single mom shows up, he tries to fix her up with Jack so that he can be part of Jack's family. He sabotages Jack's current relationship for the plan to take effect. Elliot learns that a once great photographer has been slumming at Nina's, he's now a 'down and out'. So Elliot tries to help him.