Just Shoot Me! - Season 5 (2000)

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 where 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.

Finch meets up with an old friend and is ashamed of his feelings; whilst Elliot gets back at Nina for treating her assistant badly.

Everyone will spend Thanksgiving at Jack's country house.

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.

Maya and Elliot take in a lost dog. Everything is fine until Finch convinces Elliot that Maya has gotten the dog to test his fatherhood skills. Meanwhile Jack wins the lottery but Finch never bought the ticket in the first place.

Finch dates a female boxer with a jealous ex-girlfriend. Elliott, Jack and Nina fool Maya into believing that they're smarter than she is.

Maya and Nina have a quarrel over the intentions of giving out invitations to the bridal shower.

Elliott's impulsive decision to propose to Maya has dire consequences.

Maya gives Elliott the ring back. Elliott proposes again and passes out again. Maya comes to the realization that Elliott is not interested in what she is and kicks him out of their apartment.

Elliot and Maya go on dates after their breakup. Finch tries to jeopardize the auction of Jack' collection after he feels betrayed.

Ashton Kutcher plays a new intern that Finch immediately develops a man crush on, Nina starts dating a magician who creeps everyone out and "boops" Elliot's nose, Pamela Anderson also appears.

Finch DJs a bar mitzvah for a kid who has a crush on Nina. Jack and Elliot set their sights on the same woman.

Maya and Harrison, a son of Jack's close departed friend become close. Jack gets very nervous, when he looks into the possibility that Harrison might actually be his son.

Everyone likes Nina's younger sister Erlene, who comes to New York for a visit. Nina is jealous and plots to give her the boot.

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.

Finch becomes a boy toy for a loaded, middle-aged novelist. Nina is asked to co-host the American awards.

Nina convinces Maya to stop over thinking her dating life and just go for it. Eliot tries to get Finch to do something good.

Nina pesters Eliot to set up a therapy session with his new girlfriend. Alie wants Jack back.