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.

Holly sneaks into a sorority Eden is pledging to find out why she was rejected years ago. Haskell turns the guys' apartment into a pretend AirBnB to attract a woman.

Phil’s stint on a movie set leads to romance with the female star. Holly struggles with having to fire someone for the first time.

Haskell’s estranged brother shows up and asks for one small favor: his kidney. Holly mentors a teenager who turns out to like Eden’s job more than hers.

Holly's wedding day arrives. Business partners Haskell and Nicki strike it rich.

Holly accidently convinces Stuart to quit his dental practice and buy a restaurant. Haskell, sick of paying alimony, tries to persuade his ex wife Margo to marry her fiancé.

Nicki returns, disrupting the lives of Stuart and Phil; Haskell and Eden attend a nude "Twelve Angry Men."

Phil is convinced that the woman Haskell is dating is really a man. Stuart feels guilty after sleeping with a woman who thinks that he is a war hero.

The gang attends a charity silent auction. Haskell wins a police ride-along. Phil wins dinner with his favorite sitcom TV Mom. Stuart and Holly are forced to share a cooking lesson with a celebrity chef.

Holly, over the moon, introduces the gang to her new boyfriend, Congressman Charles Hayward, but they soon begin to question his motives.

Stuart’s sister Nicki comes back from her European vacation with a female lover. Holly, inspired by Nicki, decides to try dating women.

Phil and Stuart have a fight with Haskell and he moves out. Holly, desperate to keep them all together, sends Phil and Stuart to bring him home.

Stuart's sister has shocking news about her marriage; Phil and Eden contemplate a guest in the bedroom.

Haskell hatches a plan to win over Nicki. Stuart and Phil visit Stuart's old home one last time before it is sold.

When Phil unwittingly sleeps with a nun, he must keep Nicki from finding out; Haskell and Eden care for Holly when she is injured.

Holly represents Nicki in her divorce, but lets her own history with marriage get in the way. Phil tries to prove he’s not getting older by dating a much younger woman.