Martin has trouble climaxing and is referred to a therapist. Through hypnotism, she leads him to suspect he is repressing the memory of childhood abuse.

Martin tries to seduce Judith's best friend from college, but she only has eyes for someone else…

Martin looks for a new best friend, after Eddie decides to move to LA to join a sitcom.

Under pressure from Gibby to get an elite writer, Martin attempts to lure the writer dating Toby (who coincidentally, is an award-winning author).

Martin dates a woman that acts strange in public, and yet, is an etiquette expert.

Jeremy's math teacher is the cause for Jeremy's low math grade.

Martin's life is examined after he dies.

After Jeremy chooses to go to Richard Stone's induction into the Rock N Roll Hall of Fame instead of with Martin on a Father's Day canoeing trip, Martin reluctantly tags along. In typical Tupper fashion, he goes home with a girl named Katrina that he meets there. It turns out that she has 2 interesting, but related surprises for Martin.

This picks up with Martin and Katrina struggling to write songs for the new Crevice album. Katrina suffers from a light writer's block, and ends up taking inspiration from Martin's college poetry. Crevice breaks up over the creative changes, and Katrina debuts her first single as a solo artist on Eddie's show. The fan's are not pleased.

Martin's building goes co-op, and to be able to afford purchasing his apartment/condo, he dates Gibby's insane sister.

Martin dates Judith's sister.

Toby is in a rut. Uses self-help book.

Martin needs to make some quick money, so he writes for pornographic movies.

Martin tries to get a homeless woman's memoirs.

Eddie learns that he was adopted.

Martin's friend likes Toby.

Martin and Judith visit Jeremy at college. Sparks ignite.

With their relationship rekindled, Judith suggests that she and Martin join a support group for couples on their second time around.

Martin moves into Judith's high-tech apartment.

Gibby picks Martin to represent Whitestone at the Chicago Book Fair, informing him with one weeks notice. This means a ton of extra work and pregnant Toby doesn't really feel up to it, so Martin suggests they take on a temp to lighten the load. Toby offers up her cousin Louie, and although initially reluctant, Martin assents, giving him a trial period to prove himself.

Flashback episode: Martin's fortieth birthday is approaching fast and Eddie insists on throwing him a party. Unfortunately, Judith is planning a party of her own thus bringing them into conflict. Martin suggests compromise by urging them to plan the party together. As they argue over the details, they reminisce over their past disagreements.

At a Salary Review Meeting, Gibby has some good news for Martin; Martin's to be put in charge of his own division at Whitestone, a quality publishing imprint called Camelot New Press. Things get off to a bad start however when the first round of author interviews yield nothing. Through a quirk of fate, Martin remembers an old manuscript he admired, ‘The Barrel Maker' by Julian Keppel and stays up all night reading it. He contacts the emotionally fragile author and promises to make it Whitestone's next bestseller.

Martin thinks things are getting out of hand after Judith discovers "some little tricks" to improve her sex life.

Judith plans a dinner party for their couple friends, so she suggests that Martin not invite currently single Eddie. When Eddie finds out, he makes Martin feel guilty until he invites him, but the evening doesn't go well. Eddie has nothing in common with the couples and so he storms out. Next day, Martin and Judith meet a recently separated friend, Rema, whom Martin invites to their apartment for dinner, planning to also invite Eddie and match them up. Eddie begins spending all his time with Rema and hardly sees Martin.

Martin's old apartment is becoming a huge money pit, costing him exorbitant maintenance fees and so he resolves to get rid of it. He has a meeting with Irwin Bader who isn't optimistic of getting much over $1,500, even though he sold it to Martin for $2,400. Libby expresses an interest on behalf of her son, but Martin passes on the idea.

Preparing for Eddie's wedding, Martin questions whether or not he has a future with Judith.