Holly, a divorce attorney, sets up her newly single client Stuart with fellow divorcés -- and his new roommates -- Phil and Haskell, who help him adjust to post-married life.
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Phil uses Holly's assistant, Eden, as bait to sign a star horse jockey, but the jockey only has eyes for Holly, and Haskell urges Stuart to sell his clock collection.
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Holly plays matchmaker for Stuart and accidentally sets him up with a prostitute, while Haskell embellishes his life on social media to make his ex-wife jealous.
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Haskell has Phil pretend to be him when his online girlfriend surprises him with a visit, while Stuart and Holly encounter a homeless man in the laundry room.
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Stuart's work-life imbalance shifts after Phil sleeps with his dental assistant and doesn't call her, while Holly's clothes have a better social life on Eden.
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Holly's mom (Judith Light) visits, and Holly takes over the guys' apartment because she lived there with her ex-fiancé and hasn't yet told her mom that the engagement is off.
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Stuart acts as interpreter when Phil meets a Serbian lingerie model, Haskell buys a coffin as an investment, and Holly tries to make a good impression on a neighbor.
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Stuart takes Phil to his favorite restaurant, where Phil learns his ex-wife is engaged, then later discovers her fiancé cheating, while Holly can't read a colleague's signals.
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Holly starts dating Phil's top client, an all-star basketball player (Amar'e Stoudemire), and it affects his game, while Haskell recruits Stuart into sports betting.
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Holly needs one of the guys to pretend to be her boyfriend to prove to her cheating ex-fiancé that she's moved on, while a former neighbor tells Stuart his ex-wife is engaged.