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 plays musical apartments when his building is temporarily closed for asbestos removal and he and Charlie can't bring themselves to move in together. Sam is down when he quits his job and finds out the $9,000 he invested with Matt has evaporated.

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.