Richard, Judith, Jeremy and the baby are moving to Washington D.C. Martin is despondent, but events take an unexpected turn.
Martin tries to cheer Toby up when her cat dies by buying her a replacement. When she refuses the gift, he has to keep the pet himself.
Martin's irritating mother comes to New York for plastic surgery, but things take a turn for the worst when she has a heart attack on the operating table.
Martin runs into old high school love Cheryl Castorini, but suspects she may be keeping a secret about their former relationship from him.
Unbeknownst to Martin, Jeremy uses Eddie's empty bachelor pad to attempt to score with a hot teen TV star.
Gibby takes a vacation, leaving Martin in charge of Whitestone with one simple condition – he has to fire one of the company's book editors. Judith is depressed when her patient commits suicide.
Trouble in their romantic relationship may spell the end of a book collaboration for two writers (Donna Mills and Jake Steinfeld), and it's up to Martin to help them work things out.
Toby falls in love with a priest.
Martin's girlfriend takes a job as his ex-wife's nanny.
Martin is blinded in a bizarre accident.
Martin's sister Susan wants to get married in a small ceremony without the family knowing. Nevertheless, the whole family ends up getting involved, planning a big wedding party.
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.
Martin is excited by the prospect of hooking up with an old school friend who he bumps into at Judith's birthing class, but when the irresponsible father reappears on the scene, he suddenly has a rival.
When Jeremy visits his dad's apartment to watch a movie, Martin isn't happy to discover he's had a tattoo of a skull done on his arm. Judith drops by with Jeremy's bag and Martin brings the tattoo to her attention, but she is slightly less vocal in her condemnation than Martin. Judith asks Martin to talk rationally with Jeremy, but Martin decides that punishment is a better response.
It's the Whitestone office party, and Martin is less than thrilled to be there, until he notices a hottie making eyes at him from across the room. He gets to know the woman, Alannah, better during the evening. Afterwards, Martin bumps into Gibby and is surprised when he shows off Alannah as his latest plaything. In the days following, Martin is paranoid that Gibby suspects he and Alannah are carrying on behind his back.
It's summer, and New York is experiencing a chronic heatwave. Martin is sweltering in his apartment due to broken air-conditioning. He seeks out his building's new super, a gorgeous woman named Debra. After fixing the fan, the two of them go all the way in torrid fashion, and all is well until . . .
The beautiful widow of a famous author brings a new unpublished novel by her late husband to Martin with the one caveat that he cannot reveal the true origin of the book, thus giving Toby the opportunity to accept the kudos for the bestseller.
Martin, Eddie and Judith meet up at a secluded cabin for a reunion with old friends. Martin has ongoing mutual antipathy with Allison, an old writing rival who has since gone onto fame and success as an author. Eddie is anxious at seeing Cara - a woman he slept with once and never called again, although on first meeting she doesn't recognise him except from his TV show.
Andre Williams, a militant black writer of Martin's, bemoans the lack of publicity for his new book ‘Yo! Homeboy', so Martin gets him a slot on Eddie's show. The appearance is a disaster, as Andre accuses Eddie of being ‘the world's whitest black dude'. Shortly thereafter, Eddie makes some changes in his life, trying to increase his 'blackness.'
Martin finds his bar mitzvah bonds in a closet and suddenly has extra cash. Toby encourages him to invest $5,000 in a fledgling business she is setting up offering stock tips over the phone, 555-TIPS. The business goes terribly, until a wrong number mistakes it for an S&M phone-sex chat line and stays on for hours. Seeing where the real money is, Toby employs the services of her family – Gina, Angie – in order to cover the phones.
Martin's divorced father Mickey comes back to live in New York. Martin fixes him up with Toby's mom Angie on a dinner date. He takes her home, but to Toby's irritation ‘does nothing' to her. Martin visits the one- bedroom apartment Mickey is sharing with apartment owner Roger.
Martin is disgusted by the quality of the books Gibby is forcing him to edit, and his lack of appreciation. Meanwhile, Eddie is fired from his talk show and his wife Jeanette leaves him on the same day. Eddie begins to reassess his life and Martin encourages him to make a change, proposing they collaborate on creating an up market magazine.
Martin needs to find a tenant for his empty apartment in a hurry when the other tenants renege on their agreement to move in. Meanwhile, Julie is pregnant by a French exchange student and she asks Martin to pay for an abortion. Kate confronts Martin when a bill comes from the gynecologist.
Martin gets a new video camera and inadvertently videotapes children's television celebrity Uncle Bouncy committing a sex act with a prostitute in a public alleyway. Martin opts to caution Bouncy himself about his behavior in person before turning the tape over to him. But, Bouncy's abusive and intransigent attitude convinces him to sell the offending footage to Eddie for broadcast on his show.
