Gibby informs the crew that they are all fired, just to soften the blow that there will not be bonuses (not really fired). Martin is talked into a nickel and dime porker game with his co-workers. They play in Martin's apartment. Expecting pizza, Martin finds Gibby at the door. Carter, the brown nose, had told Gibby about the game. Gibby lays down a large pile of $100s (the firm is doing financially badly, not him). All but Martin want to play high stakes, until Martin sees his cards. After losing big ($12,000), Gibby starts betting vacation days. Eventually clothing and household appliances get bet.

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.

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.

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.

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.

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.

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

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.

Gibby desires to publish Jeremy's novel.

Martin and Judith learn Dr. Stone might be defrosted and revived.

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.

An old female friend of Martin's, Bonnie, returns to New York City from Cleveland to pursue a stand-up career. Bonnie's first performance as a stand-up bombs. Martin tries to encourage her by suggesting that she should use her past relationships in her act (which has more humor in it than her current act). Martin and Bonnie start to fall for each other and end up sleeping together. The whole gang shows up for Bonnie's second performance as a stand-up comic. Bonnie, following Martin's advice, discusses her relationships in her act. Unfortunately for Martin, Bonnie sticks to talking about her current relationship. The gang, and the audience, except for Martin, love the new act. Afterwards, the gang offer Bonnie funny stories about Martin. Alone together back at Martin's apartment, Martin almost starts to tell Bonnie about his reactions to her new act. A phone call interrupts. An HBO scout was in the audience and loved the act. Next Friday, Bonnie is informed, an HBO big-wig wil

Martin's pleasure at having attractive new female neighbors is mitigated when he discovers that they are prostitutes.

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.

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 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.

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 and Eddie attend their school reunion, where Martin is eager to make up for lost opportunities with a recently-separated old flame.

Toby nurses Martin back to health.

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 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

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, 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.