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.

When the guys have differences that they can't seem to resolve, Holly suggests couples therapy for them. But her move backfires when it becomes apparent that she is the cause of their problems.

The gang's relationships are thrown out of whack when it is discovered that there is more to Stuart than originally thought.

Holly & Haskell go on a practice date. Stuart tries really hard to fit in with Phil's friend and embarrasses him in the process.

Chopin, the dog that Stuart lost custody of in his divorce, stays over. Phil then accidentally switches the dog with a look-a-like, after having a one night stand with another dog owner. Holly suspects that Eden is having an affair with their married boss, Mr. Hubner (James Morrison), and is even more convinced when she discovers that Eden is pregnant.

Phil's desire to sign top mixed martial arts fighter Tommy Dunbar (Craig Gellis) as a client has the guys all attending a strip club, which lands Stuart in the hospital. Meanwhile, Eden buys Holly a new bra, which provides surprising benefits.

Holly offers to help Stuart impress his ex-wife, Lorna (Janet Varney), at a ballroom dance contest, but it turns out Holly is no help at all. Adding insult to injury, it appears that Lorna and her partner (played by Dancing with the Stars pro Maksim Chmerkovskiy) are the favorites to win the competition. Meanwhile, Phil meets his female match, Kendra (Garcelle Beauvais), who beats him at his own game.

Holly starts to hear her biological clock ticking, so the guys help in her search for a sperm donor.

Holly's continuing crush on her co-worker Paul, makes her determined to find out how he feels about her. Meanwhile, frustrated with being the only roommate who cleans the apartment, Stuart hires a maid who begins to disrupt Haskell's life.

Holly flaunts her new boyfriend, Paul, and Paul invites the roomates to a great party. But Stuart sees signs that Paul may still be too close to his ex-wife.

With her mother, Majorie (Judith Light), and sister, Jill (Amanda Detmer), in town, Holly tries to impress her "perfect" sister by creating a new identity. Meanwhile, the guys are enamored by Stuart's cooking.

A professional tennis player and ladies man (Zach Braff) is in town, but he turns out to be more of a man's man instead.

The gang crashes a party on Phil's boss's yacht; a very pregnant Eden goes into labor.

When the guys accidentally break Holly's vibrator, they scramble to fix it before she finds out so it doesn't ruin their friendship.

Holly's boyfriend tells the guys he doesn't want them around when they're together, which forces Holly to choose between playing poker or going on a date.

Holly and Haskell fight for the affections of a beautiful woman they met at the same time. Later, Stuart and Phil are forced to admit that their first impressions of their dates were wrong.