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- A group of divorced friends tries to get back to the single life.
- Teachers show their hilariously warped perspective as six elementary school educators try to mold young minds although their own lives aren't really together.
- Buddy Dobbs (Michael Rosenbaum), a slacker on the run from a loan shark, steals a man's identity and ends up posing as a small town's new gay pastor.
- Stuart's (David Alan Basche) work life is turned upside down when Phil (Donald Faison) sleeps with his dental assistant. Holly (Kristen Johnston) lends Eden (Kelly Stables) some outfits and soon discovers her clothes have a better social life than her.
- When Holly has to face her cheating ex-fiancé 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.
- Divorce attorney Holly (Kristen Johnston) sets up newly single Stuart 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 (Donald Faison) uses Holly's assistant to help him land a star jockey as a client, but he's got his eyes on a bigger prize. Haskell (Wayne Knight) talks Stuart into selling sentimental mementos from his marriage but Stuart has trouble letting go.
- Holly (Kristen Johnston), determined to find Stuart (David Alan Basche) a date, introduces him to a woman who turns out to be a true professional. Haskell (Wayne Knight) invents a fabulous online lifestyle for himself in order to one-up his ex-wife.
- Phil (Donald Faison), Stuart (David Alan Basche), and Haskell (Wayne Knight) are forced to trade apartments with Holly (Kristen Johnston) when her mother (Judith Light) comes for a visit because Holly never told her mother her engagement ended months ago.
- Phil (Donald Faison) meets a foreign lingerie model who doesn't speak English and Stuart (David Alan Basche) has to act as interpreter. Eden helps Holly overcome a bad first impression with a handsome neighbor. Haskell buys a coffin as an investment.
- Haskell (Wayne Knight) panics when his online girlfriend surprises him with a visit, because he used Phil's (Donald Faison) picture as his own. Holly discovers a homeless man in the laundry room and learns appearances can be very deceiving.
- When Stuart's favorite restaurant is about to close, he takes Phil along for one last meal, only to bump into Phil's ex-wife who is now engaged. Holly is baffled by mixed signals from a cute co-worker. Haskell starts an online traffic school.
- Phil (Donald Faison) is nervous when Holly (Kristen Johnston) starts dating his top client - basketball player Kevin Tyler (Amar'e Stoudemire). Haskell (Wayne Knight) lures Stuart (David Alan Basche) into the world of sports betting.
- When the guys can't resolve their differences, Holly sends the three of them to couples' therapy, where they discover that Holly is the problem.
- Against his better judgment, Phil gives the gang a tour of his boss' yacht with chaotic results.
- Holly takes Haskell on a practice date, and finds herself blown away by Haskell's hidden talents. Stuart embarrasses Phil when he tries way too hard to fit in with Phil's friends.
- The gang's relationships are thrown out of whack when Holly discovers there's way more to Stuart than meets the eye.
- Holly tries to get to the bottom of a big secret between Eden and her boss. Stuart is about to be reunited with his beloved dog - until Phil loses him.
- Phil's quest to land a new client puts the boys in a strip club, and Stuart in the hospital. Holly's new "magic bra" works wonders.
- Holly volunteers to help Stuart impress his ex at a ballroom dance competition, but Holly's "talent" hurts more than it helps. Phil meets his match in a woman who beats him at his own game.
- After giving Holly's new boyfriend Paul a hard time, the guys make amends and Paul invites them to the party of a lifetime. But on the way, Stuart discovers that Paul's ex-wife might still be in the picture.
- Holly rushes to look for sperm donors when she finds out her biological clock is rounding midnight. The guys pledge to find her the perfect match--and who could be more perfect than themselves?
- Holly's office crush Paul returns to work, and she is determined to find out how he feels about her once and for all. Stuart, sick of doing all the cleaning himself hires a maid, who quickly turns Haskell's life upside down.
- Desperate to impress her perfect sister Jill, Holly invents an alternative lifestyle for herself that quickly spirals out of control. Meanwhile, the guys are riding high on a "special" dish cooked up by Stuart.
- Phil's client, tennis star Chuck Feeney, stays with the guys to hide from the paparazzi. But Chuck the ladies' man turns out to be more of a man's man. Haskell and Holly compete over who can take better care of pregnant Eden.
- When the guys accidentally break Holly's vibrator, they scramble to fix it before she finds out so it doesn't ruin their friendship.
- A group of twenty somethings and a group of seventy somethings discover they'll be living together in an experiment designed to bridge the generational gap.
- The juniors and seniors compete in a food truck challenge that exposes major differences in the way each generation approaches money.
- The juniors and seniors take a party bus to Palm Springs where they are given a chance to unwind their cares and rewind their wardrobes.
- The juniors and seniors head to Vegas to dance, gamble and reflect on their experiences together before being presented with a life changing decision.
- 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.
- 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.
- 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 practice's perfect rating.
- 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.
- 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 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.
- Eden shares a secret about herself and Phil with Holly, who blabs to Stuart and Haskell, testing boundaries within the group.
- 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.
- 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 (Leah Remini) 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 (Leah Remini) returns to start her new life in the city, disrupting Stuart's professional life and Phil's personal life. 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.
- Stuart asks Nicki to accompany him to an important dinner. Phil and Haskell consider getting vasectomies together.
- Holly accidentally sets Haskell up with a gay man. Stuart helps Phil get over his fear of funerals.
- Holly dates an older man only to find he lives in an assisted living facility. Nicki comes to Phil with a proposition.