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.

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 is a member of the audience of the ""Eddie Charles Show."" Today's topic is about the current weak nature of the male gender. Martin, inspired by the guest author of the show, decides to go away to a male-bonding workshop. At the retreat, Martin learns that he is an elephant. After a somewhat disappointing time, Martin returns home. Back in New York, Martin runs into the ""perfect woman"" (Mary) at a supermarket, and they begin a relationship. Mary cooks, cleans and takes care of Martin. Mary is very ready to help and loves to allow Martin to make all the decisions. Mary also expects and encourages Martin to have guests over to watch sporting events on television. Oddly enough, Martin is starting to find Mary grating.

Martin decides to take his first vacation in a long time, and visits a travel agent. Many expensive options are presented, and Martin settles on Bermuda. Martin is eager and happy to begin his vacation, until his boss visits him. The boss, Sid, wants to know if Martin has heard about the current tragic news circulating throughout the city. The current news story is about the gruesome murder of a family that included the butchering of their dogs. Before Martin can go on his vacation, he has to get the widow signed as an author with Whitestone. The person that would normally do this is out sick. Martin is very reluctant, but cannot say no. Martin finds himself to be rather good at this type of activity, but does not like this fact. The widow, Lyia, is not sure if she wants to drag the sordid mess out before her fellow citizens. They've hounded her enough. On the other hand, she might be tempted to tell her story. At the same time, the police have yet to find the killer.

Martin is quite interested in one of the guests, Sheila, on Eddie Charles current show ""Wall Street Witches."" Sheila and Martin have an instant connection, and Eddie is stuck right in the middle. Due to a back problem that will require surgery, Eddie is propped up in a handcart and cannot escape the sexual tension. Sheila and Martin date, and while walking along outside, Sheila asks Martin to make a wish on her crystal. Next scene: bedroom. After a rather intense experience, Sheila wants Martin to make three wishes using her crystal. Martin wishes to win the lottery, find his rare missing baseball card, and have perfect Dr. Richard Stone fail at something. The first two wishes come true, though not exactly as Martin thought they would. After realizing that there is some strange magic in the air, Martin worries that the last wish will also come true.

Martin has clothes in the dryer, and more in his arms, as he returns to the laundry room. Martin returns to find a woman that Martin has not seen before reading a book and doing her own laundry. An instant attraction is sparked in both. While chatting with the woman, Nina, Martin finds that his clothes that were in the dryer have been removed and are damp. Martin is very annoyed and expresses his rage at the idiot who removed his clothes and put their many pairs of pants into the dryer. Nina notes that Martin should have been there when the dryer was done, and she wouldn't have had to remove his clothes. Just then the dryer stops. Martin opens the door, Nina protests that the clothes are still wet, and instead of continuing the argument, Martin and Nina kiss and explore each other. The activity continues in Martin's apartment, and involves several days. Office mates, notably Toby, are annoyed at the missing Martin. While extremely happy, Martin and Nina's relationship suddenly

Despite the continuing distraction of a prior boyfriend, and the deep involvement in the protest movement, Nina and Martin are still together. Nina suggests to Martin that they take the next step in their relationship – an AIDS test.

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.

Martin's friends and family offer support after Nina's arrest, but he prefers to be alone. While resting in his apartment, Martin receives a call from Irma, a suicidal woman trying to reach 555-HELP. Martin's phone number, it turns out, is 555-HELL. As Irma wants to exit this world at midnight, and as it is only three minutes to midnight, Irma doesn't want to contact the correct phone number. Martin tries to keep her on the line, and keep her from killing herself.

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.

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.

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.

Cousin Phil visits, and informs Martin that he has split up with his wife (shrew). While in Martin's office, Phil sees Toby for the first time, and is smitten. Phil begs, and Martin helps Phil pursue Toby.

Martin, while putting away Jeremy's laundry, comes across an adult magazine and a joint. Martin informs Judith, and they agree that Martin will have a talk with Jeremy. Jeremy agrees to not smoke pot, and Martin admits that he used to smoke pot a long time ago. After Martin discusses the matter with Eddie on the basketball court, they return to Martin's apartment. Eddie spots the joint and lights up. Martin joins him.

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.

Eddie pushes an ""ugly"" sister onto Martin to score points with Marsha. The ""ugly"" sister (Chloe) has a book (""The Feminist Manifesto"") she wants Martin to read. Martin likes Chloe (who isn't actually ugly), but hates the book. Reluctant to reveal his true feelings, and hoping his publisher with reject the book, Martin passes the book to Gibby. Gibby really likes the books market potential.

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.

After walking out for cigarettes fifteen years ago, Martin's former girlfriend Veronica Sheridan finally returns. Veronica returned because she is pulling together a photo-book of all the famous men of New York. Everyone warns Martin to stay away from Veronica, but he can't help himself. Martin and Judith become worried when Veronica's photo session with Richard runs very late.

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 new girlfriend of three weeks, Charlotte, has a porn star past. Martin learns from Eddie. Charlotte reveals that her biggest secret is that she cannot drive. Martin begs to differ, and Charlotte admits to appearing in six porn videos to pay for college and is not ashamed. Martin and Charlotte try to continue their relationship despite this conflict. Martin tries to continue dating Charlotte, even though he keeps seeing her in porn star roles and settings.