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.

Haskell’s ex-wife gets amnesia after an accident; Phil and Stuart spend the night in Holly’s place.

Holly dreads dating again so the guys create an online dating profile for her.

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 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 younger man; Phil and Eden become friends with benefits; Stuart convinces Haskell to pursue a woman he is interested in.

Holly creates chaos at her ex-boyfriend's wedding, where Phil and Eden realize they're falling for each other, and Haskell preys on the desperation of female guests.

When Holly spills one of Eden's secrets to Stuart and Haskell, group boundaries are tested.

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.

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

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

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

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

Nicki is asked to accompany Stuart to an important dinner; Phil and Haskell consider vasectomies.

Holly dater en gammel mand men opdager, at han bor i en beskyttet bolig. Nicki giver Phil et tilbud.

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 er Nickis skilsmisseadvokat men lader sine egne erfaringer med ægteskab komme i vejen. Phil prøver at bevise, at han ikke er ved at blive gammel ved at date en meget yngre kvinde.

Holly slutter sig til en støttegruppe for sørgende for at møde en mand. Stuart og Haskell hjælper Phil, der er begyndt at læspe, med at forberede sig til en optræden på et talkshow.

Haskell dater en smuk kvinde, som Phil er overbevist om, i virkeligheden er en mand. Stuart bliver tynget af skyld, efter at han går i seng med en kvinde, som tror, han er en krigshelt.

Haskells bror, som han havde mistet al kontakt med, dukker pludselig op og beder om en tjeneste: Haskells nyre. Holly er mentor for en teenager, som viser sig at være mere interesseret i Edens job.

Holly holder en fødselsdagsfest for Stuart og Nicki i håbet om at imponere en ny mand, men Nicki og Stuarts far forpurrer hendes planer.

Haskell forhindres i at overvære en bowling-begivenhed, som holdes i hans ære. Holly omskriver i al hemmelighed Edens universitetsansøgning og er nær ved at ødelægge hendes drøm.

Vennerne tager til en auktion for velgørenhed, og Haskell vinder en tur i en patruljevogn. Phil vinder en middag med hans yndlingsmor fra en tv-serie, og Stuart og Holly er tvunget til at dele en madlavningslektion med en berømt tv-kok.

Holly søger optagelse i en kvindelig studenterforening, som Eden er medlem af. Haskell transformerer fyrenes lejlighed for at imponere en kvinde.

Holly introducerer vennerne for sin nye kæreste men opdager, at de stiller spørgsmålstegn ved hans motiver.

Det får alvorlige konsekvenser for Holly, da et skandaløst billede af hende bliver trykt i avisen.

Forretningspartnerne Nicki og Haskell har held i sprøjten på Hollys store dag.

Holly får en gave med et stemme-aktivere operativ system, og bliver alt for afhængig af det.

Holly er træt af alt det datingdrama, så hun beslutter sig for kun at gå efter mænd, der ikke interesserer hende.

Stuart hyrer Phil til sit acapella-kor. Holly vil have hævn.

Stuarts søster kommer tilbage fra sin ferie i Europa, med en ny kæreste... en kvinde.

Haskell flytter ud, efter at have haft et sammenstød med Phil og Stuart, men Holly kæmper en desperat kamp for at holde gruppen samlet.

Phil har en romance med en stjerne, efter en tjans på et filmsæt. Holly må, for første gang fyre nogen.

Phil laver en fejl på sin første date med en filmstjerne, så Holly er nødt til at snige sig med på den røde løber, for at redde ham ud. Stuart og Haskell konkurrerer om at få flest følgere på Twitter.

Holly og Nicki planlægger en tøsebytur, men ender med at konkurrere om den samme fyr. Phil indser at det er sværere at date en filmstjerne, end han havde troet.

Holly overtaler Stuart til at droppe sin praksis, og i stedet købe en restaurant. Haskell prøver på at overtale Margo til at gifte sig med sin forlovede.

Stuart og Holly overtaler Margo til at holde sit bryllup i restauranten. Haskell forsøger at stoppe Margos bryllup.