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Movies like Sleeping with Other People (2015)

The best movies like Sleeping with Other People (2015) are The 40 Year-Old Virgin (2005), Tootsie (1982) and The Ugly Truth (2009). If Sleeping with Other People hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The 40 Year-Old Virgin (2005)

    Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  2. Tootsie (1982)

    When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego—Dorothy Michaels—in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  3. The Ugly Truth (2009)

    A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  4. That Awkward Moment (2014)

    Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  5. Another Gay Movie (2006)

    Andy is your typical All-American eighteen-year-old gay virgin. Like everyone else, he's dying to have sex. Totally out of the closet and mad-crazy horny, this naïve high school senior is caught in that awkward vortex between child and adult. Much to the dismay of his mom (who wonders why all her carrots and cucumbers keep disappearing), Andy spends much of his private time practicing for the big moment when he'll finally take the plunge.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  6. The Knack... and How to Get It (1965)

    A nebbish schoolteacher begs his smooth (and misogynistic) pal to teach him 'the knack' – how to score with women. Serendipitously, the men meet up with a new girl in town, as well as a friendly lunatic who can’t help but paint things white.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  7. Someone Great (2019)

    An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one outrageous last adventure in New York City.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  8. American Pie (1999)

    At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score" by their senior prom.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  9. Friends with Benefits (2011)

    Dylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advantage of their mutual attraction - but without any emotional attachment.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  10. No Hard Feelings (2023)

    On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To her surprise, Maddie soon discovers the awkward Percy is no sure thing.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  11. Teacher's Pet (1958)

    The rugged editor of a city newspaper poses as a journalism student and flirts with the professor.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  12. Loverboy (1989)

    Randy Bodek works as a pizza delivery boy at Señor Pizza to make a few extra bucks. Some customers are special, though: When the order is for a pizza with extra anchovies, it means the female customers are looking for some loving. But, as Randy soon learns, life as a professional gigolo can get pretty complicated.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  13. Romance & Cigarettes (2006)

    Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval. Kitty kicks Nick out of the house, and he is forced to make some difficult decisions.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  14. She's Gotta Have It (1986)

    The story of Nola Darling's simultaneous sexual relationships with three different men is told by her and by her partners and other friends. All three men wanted her to commit solely to them; Nola resists being "owned" by a single partner.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  15. I Want You Back (2022)

    Peter and Emma thought they were on the precipice of life’s biggest moments – marriage, kids, and houses in the suburbs – until their respective partners dumped them. Horrified to learn that the loves of their lives have already moved on, Peter and Emma hatch a hilarious plan to win back their exes with unexpected results.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  16. Playing It Cool (2014)

    A young man meets and instantly falls in love with an engaged woman.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  17. Mr. Jealousy (1998)

    After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  18. Plan B (2021)

    After a regrettable first sexual encounter, a straight-laced high school student and her slacker best friend have 24 hours to hunt down a Plan B pill in America's heartland.

    Why it matches: Recommended by TMDB viewers · both comedy

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  19. Old School (2003)

    Three friends attempt to recapture their glory days by opening up a fraternity near their alma mater.

    Why it matches: Recommended by TMDB viewers · both comedy

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  20. Honor Society (2022)

    Honor is an ambitious high school senior whose sole focus is getting into Harvard, assuming she can first score the coveted recommendation from her guidance counselor, Mr. Calvin. Willing to do whatever it takes, Honor concocts a Machiavellian-like plan to take down her top three student competitors, until things take a turn when she unexpectedly falls for her biggest competition, Michael.

    Why it matches: Recommended by TMDB viewers · both comedy

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  21. Bend It Like Beckham (2002)

    Jess Bhamra, the daughter of a strict Indian couple in London, is not permitted to play organized soccer, even though she is 18. When Jess is playing for fun one day, her impressive skills are seen by Jules Paxton, who then convinces Jess to play for her semi-pro team. Jess uses elaborate excuses to hide her matches from her family while also dealing with her romantic feelings for her coach, Joe.

    Why it matches: Similar story and style · both comedy & romance

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  22. Monsoon Wedding (2001)

    A stressed father, a bride-to-be with a secret, a smitten event planner, and relatives from around the world create much ado about the preparations for an arranged marriage in India.

    Why it matches: Similar story and style · both comedy & romance

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  23. Mambo Italiano (2003)

    When an Italian man comes out of the closet, it affects both his life and his crazy family.

    Why it matches: Similar story and style · both comedy & romance

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  24. About the Looking for and the Finding of Love (2005)

    Director helmut Dietls and Patric Susskinds illustrate a legendary story of two lovers who cant keep themselves away from death.

    Why it matches: Similar story and style · both comedy & romance

  25. Go for Zucker (2004)

    Germany director Dani Levy filmed this comedy about Jewish life in today’s Germany along side the familiar east-west conflict. With it great success this film is a joyful comedy of humor and knowledge.

    Why it matches: Similar story and style · both comedy

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  26. 36 Fillette (1988)

    A 14-year-old pursues romance with a man while vacationing with her family in Switzerland.

    Why it matches: Similar story and style · both romance

  27. Grill Point (2002)

    Christian is a presenter at a small radio station. His wife Katrin directs traffic in a car park. Both are friends with Uwe, who runs a fast food kiosk, and Ellen, who works in a perfume shop. Their four lives are stuck in a rut. Until the day Chris and Ellen sleep together and upset the balance of the two couples...

    Why it matches: Similar story and style · both comedy

  28. Wild at Heart (1990)

    Young lovers Sailor and Lula hit the road to start a new life together away from the wrath of Lula’s deranged, disapproving mother, who has hired a team of hitmen to cut the lovers’ surreal honeymoon short.

    Why it matches: Similar story and style · both romance

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  29. Night on Earth (1991)

    A quintet of cabbies in five cities and their remarkable fares on the same eventful night.

    Why it matches: Similar story and style · both comedy

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  30. Cockles and Muscles (2005)

    Crustacés et coquillages is a fresh French comedy film with numerous surprise turnarounds and about the tolerance of a family of four. The family spend an idealistic summer vacation together where each of the family members gets involved in a new or old relationship.

    Why it matches: Similar story and style · both comedy

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Like Sleeping with Other People and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Sleeping with Other People?

The closest matches to Sleeping with Other People are The 40 Year-Old Virgin (2005), Tootsie (1982) and The Ugly Truth (2009). Below are 27 more, each with the reason it matches.

What should I watch after Sleeping with Other People?

Start with The 40 Year-Old Virgin (2005), the closest match to Sleeping with Other People.

What is the highest-rated movie like Sleeping with Other People?

Night on Earth (1991), rated 7.5/10 by 1,110 TMDB users.

What is the newest movie like Sleeping with Other People?

No Hard Feelings (2023) is the most recent release on this list.

Are there English movies like Sleeping with Other People?

Yes: The 40 Year-Old Virgin (2005), Tootsie (1982) and The Ugly Truth (2009).

How are movies similar to Sleeping with Other People chosen?

First come films that Trakt’s viewers watch alongside Sleeping with Other People, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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