Charlie leaves Jonathan for Dennis Rodman. TV commercial singer Marie moves into Jonathan's old apartment. Sam has problems with a consultant at the studio.

Jonathan confronts a columnist after she writes a scathing review of his book. Sam and Trudy try to beat a Three Card Monte dealer, Freaky Lou. Matt tries to write a poem for Janeane for their fifth anniversary.

Jonathan pursues Charlie McCarthy, even following her to Seattle in the hopes of starting a relationship. Meanwhile, Sam, Trudy, Janeane, and Matt discover the sensuous powers of Jonathan's apartment.

Sam and Trudy watch Sebastian, Matt and Janeane's child, for a night to see if they're ready for parenthood. Sam and Trudy impulsively take Sebastian to Madison Square Garden to see a boxing match and pay the price for their recklessness when they're trapped on the subway.

Jonathan discovers that his dad's new fiancée is one of his old lovers. Meanwhile Sam discovers an old recording that he thinks is by the Beatles.

Jonathan fears he's the victim of a set-up when he breaks up with a woman with an overly protective family of cops. Trudy tries to buy an illegal Cuban bra.

Jonathan is coerced into being the best man at the wedding of a man he hardly knows. The bride confides in Jonathan that she doesn't want to get married and asks Jonathan to tell the groom. Trudy throws out Sam's lucky sneakers.

Jonathan discovers everything falling into place in his life when he writes the Sunday sermons for a dull preacher. Sam suffers from back pain which is alleviated when he attends church. Trudy spends all her time at a firing range.

Jonathan is a 'kept man', running errands for his new girlfriend in exchange for presents and other perks. Sam obsesses when he finds out that Trudy makes more money than him.

Jonathan and Marie look for employment at a temp agency. Sam hides the truth from Trudy when he visits a strip club.

While riding the subway on his way to a Halloween costume party, Jonathan meets the girl of his dreams dressed in a Cinderella costume. Jonathan places an ad in the newspaper and rides the subway to find her again. Russell studies for a law exam.

Trudy hires Jonathan to deliver an art exhibit, The Virgin, by Carl Gannon (ep #12). It turns out 'the virgin' is a beautiful woman. Jonathan desperately tries to make the delivery without damaging the goods. Sam and Marie make special effects for a B-movie.

Jonathan takes Marie out on her wedding anniversary. Trudy's parents visit, giving Sam conniptions. Trudy has dinner with her first true love.

Jonathan visits a therapist as part of his New Year's resolution. The therapist urges Jonathan to forsake women until he decides what he really wants with his life. Sam and Trudy agree to work on starting a family.

Jonathan gets an advertising job. Jonathan goes along with new neighbor Dan on an all-night binge against his better judgment.

Jonathan and Dan compete for the love of a woman, Bambi. Trudy forces Sam to throw out his junk.

Jonathan thinks it is fate when he keeps running into the same woman, until he discovers it's Manny's engaged granddaughter. Jonathan tries to weasel out of it when she calls off her wedding, apparently to marry Jonathan. Dan and Marie have a cross-dressing contest.