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.

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.

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.

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.

Holly joins a grief support group to meet a man. Stuart and Haskell help prepare Phil for a talk show appearance after he develops a lisp.

Stuart recruits Phil for his a cappella group and Phil leads a rebellion. Haskell leaves Holly out of his will and she seeks revenge.

Holly and Nicki plan a girls’ night out, but wind up competing for the same guy. Phil realizes dating a movie star is much more difficult than he imagined.

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.

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.

When Phil and Holly make a pact to ask their bosses for raises, Phil gets fired. Holly tries to help Phil get his job back. Stuart's integrity is tested when he dates a British woman with repulsive teeth.

Holly convinces everyone to spend Christmas together, but then ditches the group.

Holly sets Haskell up with a man; Stuart tries to help Phil conquer his fear of funerals.