Most Similar Movies to Happy Endings (2005)
If you are looking for movies like Happy Endings (2005), you might like movies tagged with keyword : comedy, romance, independent film, multi-narrative, american film, 2000s, lgbtq+, deception, los angeles, relationships, humor, emotional entanglements, ensemble cast, sexuality, coming of age, secrets, unplanned pregnancy, complex relationships, dark comedy, social satire .
Three of Hearts (1993), Mango Kiss (2003), Boys on the Side (1995), California Suite (1978), Year of the Dog (2007), Love in the Time of Money (2002), The Broken Hearts Club (2000) ... Let's take a look at the following list...

Three of Hearts (1993)
A lesbian hires a male escort to her sister's wedding. She thinks of a scheme to get her ex-girlfriend back: he dates and dumps the ex.
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Mango Kiss (2003)
"Mango Kiss" is a story about Lou whose world turns upside-down when she falls in love with her best friend Sassafras. They journey to San Francisco and stumble into the wild world of role-playing and non-monogamous S/M dykes. Comedy ensues as these wholesome girls get in over their heads.
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Boys on the Side (1995)
Robin shares a ride in her car from NYC to LA with Jane. They stop at Jane's friend's place in Pittsburg and take her with them west, making a long stop in Tucson. The 3 very different women become close friends.
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California Suite (1978)
Misadventures of four groups of guests at the Beverly Hills Hotel.
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Year of the Dog (2007)
A secretary's life changes in unexpected ways after her dog dies.
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Love in the Time of Money (2002)
New York serves as a backdrop for a cast of characters in search of love, lust or lucre including a woman who makes awkward moves on the man renovating her SoHo loft, an embezzler, a sleazy artist and a phone psychic.
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The Broken Hearts Club (2000)
An insight into the turbulent lives and loves of a gay clique based in Los Angeles.
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Barry Munday (2010)
Barry Munday wakes up after being attacked to realize that he's missing his family jewels. To make matters worse, he learns he's facing a paternity lawsuit filed by a woman he can't remember having sex with.
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The Best Man (1998)
A pretty Italian (Ines Sastre) weds a wealthy businessman (Dario Cantarelli) while pledging herself to his best man (Diego Abatantuono).
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Afternoon Delight (2013)
Rachel tries to spice up her marriage with a trip to a strip club. She befriends McKenna who gave her a lapdance. She moves in with Rachel's family and becomes a nanny for the son.
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I Love You Both (2016)
Krystal and her twin brother/roommate confront twenty-eight years of their codependency when they start dating the same guy.
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But I'm a Cheerleader (1999)
A naive teenager is sent to rehab camp when her straitlaced parents and friends suspect her of being a lesbian.
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The Brothers (2001)
Four friends (Morris Chestnut, D.L. Hughley, Bill Bellamy) question women, relationships and honesty after one of them becomes engaged.
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The Opposite of Sex (1997)
A 16-year-old girl visits her gay half-brother and ends up seducing his boyfriend, thus wreaking havoc on all of their lives.
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Fading Gigolo (2013)
Fioravante decides to become a professional Don Juan as a way of making money to help his cash-strapped friend, Murray. With Murray acting as his "manager", the duo quickly finds themselves caught up in the crosscurrents of love and money.
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The Escort (2016)
Desperate for a good story, a sex-addicted journalist throws himself into the world of high-class escorts when he starts following a Stanford-educated prostitute.
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The Good Guy (2009)
Calm and quiet Daniel starts on Wall Street. His womanizing colleague, Tommy, encourages him to meet women. He unknowingly meets Tommy's girlfriend, Beth, and ends up in her 5 women book club. Will he find the woman?
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Chuck & Buck (2000)
A man (Chris Weitz) finds himself stalked by a mentally impaired friend (Mike White) from childhood who is all alone now that his mother/caretaker has died.
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