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.

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.

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.

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.

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.

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.