Martin Tupper, éditeur new yorkais plus proche de la quarantaine que de la trentaine, fait face à une crise existentielle. Sa femme Judith lui demande de signer les papiers du divorce, qui trainent depuis 2 ans, afin qu'elle puisse se remarier avec Richard. Mais Martin espère toujours reconquérir le coeur de sa future ex-femme, n'hésitant pas à idéaliser leur mariage qui fut en réalité une véritable catastrophe. Eddie, son meilleur ami, véritable coureur de jupons, lui conseille de tourner la page et de se lancer à l'assaut d'autres femmes. Mais les premiers rendez-vous s'avèrent désatreux...

During the filming of a movie about Judith's husband, Martin falls for the actress playing Judith, and Judith falls for the actor playing Richard.

Conclusion. Things heat up on the set of the Richard Stone biography, as the stars fall for each other.

Toby is plagued by nightmares in which she murders Martin in gruesome scenes of violence.

Eddie invites Martin to a Talk Show Digest awards night, where they are both approached by a beautiful woman called Alisha.

Martin does battle with a rat.

Martin gets a new video camera and inadvertently videotapes children's television celebrity Uncle Bouncy committing a sex act with a prostitute in a public alleyway. Martin opts to caution Bouncy himself about his behavior in person before turning the tape over to him. But, Bouncy's abusive and intransigent attitude convinces him to sell the offending footage to Eddie for broadcast on his show.

When Jeremy visits his dad's apartment to watch a movie, Martin isn't happy to discover he's had a tattoo of a skull done on his arm. Judith drops by with Jeremy's bag and Martin brings the tattoo to her attention, but she is slightly less vocal in her condemnation than Martin. Judith asks Martin to talk rationally with Jeremy, but Martin decides that punishment is a better response.

Gibby takes a vacation, leaving Martin in charge of Whitestone with one simple condition – he has to fire one of the company's book editors. Judith is depressed when her patient commits suicide.

Toby nurses Martin back to health.

Eddie plays the lead role in Martin's play.

Martin tries to get his son to convert to Judaism.

Mickey (Martin's father) moves into Martin's place.

Martin's life is examined after he dies.

Martin dates Judith's sister.

Martin needs to make some quick money, so he writes for pornographic movies.

Eddie learns that he was adopted.

Martin moves into Judith's high-tech apartment.