Martin Tupper, New York book editor and product of the first television generation, faces a crisis: his ex-wife-to-be, Judith, is demanding that he sign their divorce papers so that she can re-marry. Should he try to win her back, or is it time to get back in the dating game?

Martin, while fooling around with a much younger college girl (an Eddie Charles hook-up), ends up in the hospital. His doctor instructs him to change his lifestyle around to prevent another (possibly worse) incident. Top of the list? Cut out caffeine. Of course, he receives a lot of ridicule as he goes about this.

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.

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.

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.

Australians have bought Whitestone, and great change is in the air. Gibby Fiske makes his first appearance as the new boss at Whitestone, and he doesn't want to publish literature. Gibby calls Whitestone employees into his office, one at a time. Most of Whitestone's employees suddenly find themselves ex-employees. At his meeting with Gibby, Martin mentions many books, but all are too literary, not sleazy enough. Finally, and desperately, Martin states that he can get the autobiography of the host of the sleazy Eddie Charles Show. Martin begs Eddie and Eddie admits that if he did write an autobiography, he would go to a larger publisher. After more begging, Eddie eventually agrees to allow Whitestone to publish his life story. Conflict erupts when Martin seems to be leaning towards the more scandalous stories.

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.

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's romance with Sandra comes to an abrupt halt when he learns that she is the wife of a candidate for the Senate.

Martin decides to date Sandra regardless of the consequences.

Gibby convinces a reluctant Martin that the big Xmas book should be the memoirs of a gay man dying of AIDS.

Martin and Judith take a pre-Xmas drive and get stranded in a barn, Eddie is stood up by a girlfriend and spends Xmas in a bar with Santa Claus, Toby wants to become a nun and Jeremy's special Xmas present from his girlfriend doesn't quite go according to plan.

Martin and Judith take a pre-Xmas drive and get stranded in a barn, Eddie is stood up by a girlfriend and spends Xmas in a bar with Santa Claus, Toby wants to become a nun and Jeremy's special Xmas present from his girlfriend doesn't quite go according to plan.