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 Paul orders the guys to not hang out with her when he's around. When Holly discovers what Paul did, she's forced to choose between poker night and date night.
Holly and Haskell compete for the affections of a woman who they both want to be a girlfriend. Stuart dates a sensitive woman and Phil dates a physical one when they discover that first impressions aren't always right.
When Holly despairs about dating again, the guys secretly create an online dating profile for her and discover what dating is like from a woman's perspective.
Haskell's ex-wife Margo gets amnesia after an accident and stays with Haskell to recover, only she thinks they're still married. Phil and Stuart spend the night in Holly's place and get to know her intimate sleeping behavior.
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.
When Holly and Eden date two charming French men who shower them with gifts and glamorous living, they wonder if their dream dates are too good to be true. Phil and Haskell train Stuart on how to confront a bully at the bar.
Phil opens his own agency and enlists Eden as his temporary assistant to help sign his first client. Meanwhile, Holly hires Haskell as her temporary assistant. Stuart pursues the Yelper who smeared his practices perfect rating.
Holly dates a much younger man and Eden questions his motives. Phil and Eden secretly become friends with benefits. Stuart convinces Haskell to pursue a woman he's admired from afar and ends up accidentally stealing her cat.
Holly attends her ex-boyfriend Paul's wedding and throws it into chaos. At the wedding Phil and Eden realize they're developing feelings for each other. Haskell sets his sights on the most desperate woman at the wedding.
Eden shares a secret about herself and Phil with Holly, who blabs to Stuart and Haskell, testing boundaries within the group.
Holly convinces the gang to give up their Christmas plans to spend the holiday together, but ditches the group when she meets a handsome stranger.
Stuart's sister, Nicki shows up with some shocking news about her marriage. Phil and Eden consider bringing a guest into the bedroom.
Phil and Eden's relationship is strained when he is named one of the top ten bachelors in New York City and has to pretend to be single. Stuart dates the twin sister of his evil ex, Sabrina.
Nicki returns to the city to start her new life, but her move proves to be a distraction for Stuart at work and a disruption of Phil's personal life. Meanwhile, Haskell and Eden attend an all-nude production of "Twelve Angry Men."
Haskell hatches a plan to win over Nicki. Stuart and Phil visit Stuart's old home one last time before it is sold.
Phil unknowingly sleeps with a nun and must keep Nicki from finding out. Haskell and Eden take care of a fussy Holly after she suffers an injury.
Holly accidentally sets Haskell up with a gay man. Stuart helps Phil get over his fear of funerals.
Stuart asks Nicki to accompany him to an important dinner. Phil and Haskell consider getting vasectomies together.
While Holly tries to get her groove back, Haskell finds out that Phil and Nikki are planning to take their relationship to the next level. In an attempt to stop them, Haskell does the unthinkable.
In the wake of Haskell declaring his love for Nicki, Holly tries to play cupid. Stuart secretly arranges for Phil to get together with his high school crush.
Holly represents Nicki in her divorce, but her history gets in the way.
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.
Phil is convinced that the woman Haskell is dating is really a man; Stuart feels guilty.
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 throws a birthday party for Stuart and Nicki, but her real motive is to impress a guy.
Haskell is quarantined with Phil and Stuart; Holly secretly rewrites Eden's college paper.
The gang attends a silent auction for charity; Haskell wins a police ride-along; Phil gets a dinner.
Holly sneaks into a sorority that Eden is pledging, hoping to learn why she was rejected years ago.
Holly introduces everyone to her new boyfriend, Congressman Charles Hayward.
When a scandalous picture of Holly shows up in the newspaper, her engagement is put in jeopardy.
Holly's wedding day arrives; business partners Haskell and Nicki strike it rich.
After receiving a voice-activated operating system as a gift, Holly becomes overly attached to it; Haskell comes into money and controls Phil and Stuart with it.
Tired of dating drama, Holly decides to only pursue men she is not interested in; Haskell takes all of his money out of the bank.
Phil leads a rebellion after Stuart recruits him for his a cappella group. Also, Haskell angers Holly when he leaves her out of his will.
Stuart's sister returns from her European vacation with a female lover, which inspires Holly to start dating women.
Haskell moves out after a fight with Phil and Stuart, but Holly forces them to bring him back.
Phil begins dating an actress following a stint on a movie set while Holly has to fire someone for the first time.
Phil makes a mistake on his first date, so Holly must infiltrate the red carpet to help him; Stuart and Haskell compete for Twitter followers.
Holly and Nikki compete for a guy on a girls' night out; Phil realizes that dating a movie star is more difficult.
Holly convinces Stewart to quit his practice and buy a restaurant; Haskell tries to persuade Margo to marry her fiancé.
Stuart and Holly convince Margo to hold her wedding at the restaurant; Haskell tries to stop the wedding of Margo
