Jeremy (Martin and Judith's son) is having trouble in school. He has become distracted by his rather attractive female teacher. The teacher informs Judith, and Judith informs Martin. Martin tries to give his son the ""sex talk,"" but learns that Jeremy has already been informed, though he does have some questions. Martin visits the classroom and meets with Jeremy's teacher and is himself distracted with her beauty. Martin and the teacher go out for dinner.

Martin's globetrotting sister suddenly arrives in New York and visits Martin at his office. Martin informs Eddie of Susan's return, and he asks Eddie to show Susan the city. Eddie has almost no problem with this request. Eddie and Susan have been dating for eight years, and Eddie is nervous about letting Martin become aware of their relationship. Susan prefers letting Martin in on the secret, and lets the cat out of the bag by not returning to Martin's apartment (where she was supposed to be staying). Martin still sees his sister as a young girl and cannot accept that she can take care of herself, especially with noted ladies man Eddie Charles. Martin and Eddie have a falling out over this issue, and Susan refuses to be treated like a little girl.

While eating in a cheap diner, Martin and Eddie are surprised to see an old school friend as their waitress. The three of them discuss their current position in life, and where they expected to be at this point. All are depressed. Martin was going to become a writer, but had to give it up for a paying job for the sake of his relationship with Judith.

Inspired after remembering his dreams, Martin tries writing again. After several very detailed attempts, shown through old clips, Martin finally finds his subject. While some names have been changed, Martin ends up writing a rather negative play about his marriage with Judith. Martin shares his new play with Judith, and she is somewhat disappointed. Willing to accept help, Martin and Judith rewrite the play. After they finish, Martin sends out numerous copies. All but one send back rejections. One off-broadway, experimental theater offers to perform the play (oddly enough, the theater that their waitress works for). The whole g

Martin's apartment building is undergoing renovations, and there is a large hole in his outside wall. A thin sheet of plastic cannot block birds from entering the apartment. Bricks are set up to fill in the hole, but the landlady fired the contractors. Martin and Nina try to have a romantic dinner in Martin's apartment, but an emergency protest comes up, and Nina needs to join it. Nina uses the bricks from the apartment to fill up a factory's drainage pipe, and is arrested.

One of Martin's authors, Vernon, discusses his romance book with Martin. While Vernon is still in the office, a woman enters. Vernon hits on her and leaves. After he leaves, Martin reveals that he hates his job. The woman turns out to be Martin's new boss. The new boss seduces Martin. Later, at a group meeting with the staff and the new boss, Martin learns that there are some advantages to dating your boss. Martin is given a coveted book assignment, and his hated author is transfered to Cindy. Later, Martin receives further rewards for dating his boss.

Judith and Richard Stone are about to be married, but Richard is off somewhere helping the less fortunate and Judith is frantically trying to make every thing perfect for the perfect Richard Stone. After getting a bad new hair cut (frizzy perm), Judith turns to Martin for help. Judith and Martin sleep together, and Martin hopes this might mean something more. Martin reminds Judith that she acted this way before they married (and luckily, the man she slept with before their marriage was Martin). Judith, somewhat less flustered, gets married to Richard Stone.

Martin has gone on many dates after Judith and Richard's wedding, but he can never seem to perform. After discussing the problem, reluctantly, with Judith, Martin decides to go see a shrink. While paying for the first session, Martin spots an attractive woman also paying her bill. They ride the elevator together, and after Martin saves her from choking, they hook up. Judith treats the woman, and runs into an ethical problem, as she knows that the woman has a problem with rage.

After Eddie and Martin are mugged twice, Martin gets a gun. The night he comes home with the gun, Martin surprises a burglar and holds him off with the gun. While waiting for the police to arrive, Martin feeds the burglar.

An old professor of Martin's offers Martin his own show, called ""Book Beat"", on public television. The show is run by college students for credit. After the first airing of the show, Martin is stalked by an over-enthusiastic fan (Nora) who sends him flowers and other things. Nora storms the set with a bomb.

Martin and Judith are audited by the IRS for the last year of their marriage. They go through old receipts together. An old receipt proves that Martin had an affair with Nicki Rosen, Judith's friend, while still married to Judith. Jeremy wants to go to a party that lacks parental supervision, but his parents won't allow him. Martin and Judith fight about the affair during audit at the IRS office. Jeremy uses the conflict to trick his parents so that he could go to the party. At the party, Jeremy plays spin the bottle.

Martin falls for Judith's new housekeeper (Salma Hyack).