Divorce attorney Holly (Kristen Johnston) sets up newly single Stuart with also divorced roommates: Phil (Donald Faison) and Haskell (Wayne Knight). After a rocky start with Stuart the unlikely team helps him come to terms with his new unmarried life.

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Phil (Donald Faison) uses Holly's assistant to help him land a star jockey as a client, but he's got his eyes on a bigger prize. Haskell (Wayne Knight) talks Stuart into selling sentimental mementos from his marriage but Stuart has trouble letting go.

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Holly (Kristen Johnston), determined to find Stuart (David Alan Basche) a date, introduces him to a woman who turns out to be a true professional. Haskell (Wayne Knight) invents a fabulous online lifestyle for himself in order to one-up his ex-wife.

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Haskell (Wayne Knight) panics when his online girlfriend surprises him with a visit, because he used Phil's (Donald Faison) picture as his own. Holly discovers a homeless man in the laundry room and learns appearances can be very deceiving.

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Stuart's (David Alan Basche) work life is turned upside down when Phil (Donald Faison) sleeps with his dental assistant. Holly (Kristen Johnston) lends Eden (Kelly Stables) some outfits and soon discovers her clothes have a better social life than her.

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Phil (Donald Faison), Stuart (David Alan Basche), and Haskell (Wayne Knight) are forced to trade apartments with Holly (Kristen Johnston) when her mother (Judith Light) comes for a visit because Holly never told her mother her engagement ended months ago.

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Phil (Donald Faison) meets a foreign lingerie model who doesn't speak English and Stuart (David Alan Basche) has to act as interpreter. Eden helps Holly overcome a bad first impression with a handsome neighbor. Haskell buys a coffin as an investment.

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When Stuart's favorite restaurant is about to close, he takes Phil along for one last meal, only to bump into Phil's ex-wife who is now engaged. Holly is baffled by mixed signals from a cute co-worker. Haskell starts an online traffic school.

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Phil (Donald Faison) is nervous when Holly (Kristen Johnston) starts dating his top client - basketball player Kevin Tyler (Amar'e Stoudemire). Haskell (Wayne Knight) lures Stuart (David Alan Basche) into the world of sports betting.

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When Holly has to face her cheating ex-fiancé for the first time since they broke up, she enlists the guys' help to prove to him he lost the best thing he ever had.

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