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.
Manny is fired when the tenant association votes to install a security system. Meanwhile Janeane and Matt's building fires their doorman for sloppy work. Sam borrows money from a fraternity to invest in a 'trapezoid scheme'
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.
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.
Dan decides to be 'just friends' with Marie. Manny sprains his ankle and moves in with the Sloans, teaching them what a child will be like. Jonathan dates the boss's daughter and has to accept her stupid idea for an advertising campaign.
Sam and Trudy hire an au pair to watch Teddy. They do everything they can to sabotage her dream of being a professional singer when it means losing their immaculate apartment. Dan sues Manny when a water pipe in his apartment bursts.
The gang travels to Las Vegas to watch Marie portray Cher in a lounge act. Trudy loses thousands of dollars, and Jonathan wakes up from a drunken stupor holding a marriage certificate and wearing a wedding ring.
Jonathan is initially excited when a movie company that wants him to adapt his novel into a movie starring Leonardo DiCaprio approaches him; however, when it's converted to a movie starring Sinbad as identical twins; he's concerned about his artistic integrity. Sammy plays in a rock group, "Fantastic Sam and the Toads" and finds it difficult when Trudy intervenes.moreless
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.
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 falls for a TV commercial actress, the 'Butter Girl'. He gets an opportunity to meet her, only to find she only speaks French. Oddly enough she goes home with Jonathan, even though they don't understand a word the other says. Trudy throws Sam out when he tells a deeply embarrassing story about her.moreless
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.
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 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.
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 dates a fabulous girl only to discover she's only 19-years-old. Janeane ventures to a tattoo parlor to prove she's still hip and 'with it'. Sam and Trudy house an 'artist' who steals objects and calls it art.
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