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Divorce attorney Holly (Kristen Johnston) sets up newly single Stuart (David Alan Basche) 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.
Phil uses Holly's assistant to help him land a star jockey as a client, but hes got his eyes on a bigger prize. Haskell talks Stuart into selling sentimental mementos from his marriage but Stuart has trouble letting go.
Holly, determined to find Stuart a date, introduces him to a woman who turns out to be a true professional. Haskell invents a fabulous online lifestyle for himself in order to one-up his ex-wife.
Haskell panics when his online girlfriend surprises him with a visit, because he used Phil's picture as his own. Holly discovers a homeless man in the laundry room and learns appearances can be very deceiving.
Phil is reluctant to have Stuart fix his tooth, due to his fear of dentists. He finally visits Stuart's office, then sleeps with Stuart's long-time dental assistant, Deanna. Eden borrows Holly's clothes to go clubbing.
Holly's mother, Marjorie (Judith Light) visits, with Holly having yet to tell her that she is no longer engaged. So in an attempt to delay telling her mother the truth, Holly moves back into the apartment she shared with her ex, while the boys stay at her place.
Phil dates Tatiana, a Serbian lingerie model who can only speak her native language. Phil asks Stuart to be her translator, until she becomes attracted to Stuart as well. Holly keeps making a fool of herself in front of a guy she likes. Haskell buys something very strange.
Phil learns that his ex-wife is getting married and that he will no longer need to alimony, making him ecstatic. Holly tries to get romantic with her boss
Holly begins dating basketball player Kevin Tyler (Amar'e Stoudemire), one of Phil's clients. Until their sexual encounters interferes with Kevin's performance on the court. Haskell and Stuart get into sports betting.
When Holly has to face her cheating ex fiance 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.