Season 2

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.

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.

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 arrives at work to find Toby extremely happy. Martin questions her happiness, and Toby notes that it is her birthday. Martin's in trouble for forgetting, but can get out of it if he uses Toby's gift suggestions. Toby plans on celebrating her day with many activities, but strange currents are running against her (surprise wedding; many business calls; measles). Martin has to go to a wake for his Aunt Minnie, and Toby, sad that her day has been ruined, decides to join Martin. At the wake, Toby learns that Aunt Minnie is beginning to sound a lot like her. Considering the remarks made, and life described, Toby becomes rather sad. As Martin tries to lift Toby's mood, Toby responds relatively well. Then things take a turn for the worse. Then things turn ugly. Toby and Martin arrive back at work the next day very hung over.