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Movies Like The Heartbreak Kid

If you liked The Heartbreak Kid (1972), a romance and comedy movie directed by Elaine May, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1Along Came Polly

    Along Came Polly (2004)

    ★ 6/10Also comedy and romance

    Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's…

  2. 2It Happened One Night

    It Happened One Night (1934)

    ★ 7.8/10Also comedy and romance

    A runaway heiress makes a deal with the rogue reporter trailing her but the mismatched pair end up stuck with each other when their bus leaves them behind.

  3. 3My Best Friend's Wedding

    My Best Friend's Wedding (1997)

    ★ 6.6/10Also comedy and romance

    When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the…

  4. 4Wedding Crashers

    Wedding Crashers (2005)

    ★ 6.5/10Also comedy and romance

    John and his buddy Jeremy are emotional criminals who know how to use a woman's hopes and dreams for their own carnal gain. Their modus operandi: crashing weddings. Normally, they meet guests who want to toast the…

  5. 5Cousins

    Cousins (1989)

    ★ 6/10Also comedy and romance

    When Larry and Maria learn that their respective spouses are cheating on them, they try to turn the tables on them by pretending to have an affair. However, they soon find themselves falling in love.

  6. 6What Happens in Vegas

    What Happens in Vegas (2008)

    ★ 6.1/10Also comedy and romance

    During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal…

  7. 7Everyone Says I Love You

    Everyone Says I Love You (1996)

    ★ 6.4/10Also comedy and romance

    A New York girl sets her father up with a beautiful woman in a shaky marriage while her half sister gets engaged.

  8. 8The Wedding Singer

    The Wedding Singer (1998)

    ★ 6.8/10Also romance and comedy

    Robbie, a local rock star turned wedding singer, is dumped on the day of his wedding. Meanwhile, waitress Julia finally sets a wedding date with her fiancée Glenn. When Julia and Robbie meet and hit it off, they find…

  9. 9Yoh! Bestie

    Yoh! Bestie (2026)

    ★ 6.2/10Also romance and comedy

    Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.

  10. 10Love, Weddings & Other Disasters

    Love, Weddings & Other Disasters (2020)

    ★ 6/10Also romance and comedy

    A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.

  11. 11The Philadelphia Story

    The Philadelphia Story (1940)

    ★ 7.5/10Also comedy and romance

    When a rich woman's ex-husband and a tabloid-type reporter turn up just before her planned remarriage, she begins to learn the truth about herself.

  12. 12My Favorite Wife

    My Favorite Wife (1940)

    ★ 7/10Also comedy and romance

    Years after her ship disappeared, a presumably dead woman returns home. To her shock, she finds her husband has remarried.

  13. 13Housesitter

    Housesitter (1992)

    ★ 6.2/10Also comedy and romance

    Con artist Gwen moves into Newton's empty home without his knowledge and begins setting up house, posing as his new wife.

  14. 14Grumpier Old Men

    Grumpier Old Men (1995)

    ★ 6.5/10Also romance and comedy

    A family wedding reignites the ancient feud between next-door neighbors and fishing buddies John and Max. Meanwhile, a sultry Italian divorcée opens a restaurant at the local bait shop, alarming the locals who worry…

  15. 15The Out-of-Towners

    The Out-of-Towners (1999)

    ★ 5.8/10Also comedy and romance

    The adventures of married couple Henry and Nancy Clark, vexed by misfortune while in New York City for Henry's job interview.

  16. 16Blind Date

    Blind Date (1987)

    ★ 6/10Also comedy and romance

    When bachelor Walter Davis is set up with his sister-in-law's pretty cousin, Nadia Gates, a seemingly average blind date turns into a chaotic night on the town. Walter's brother, Ted, tells him not to let Nadia drink…

  17. 17The Rebound

    The Rebound (2009)

    ★ 6.5/10Also romance and comedy

    Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Aram to be her nanny…

  18. 18The Other Woman

    The Other Woman (2014)

    ★ 6.4/10Also comedy and romance

    After discovering her boyfriend is married, Carly soon meets the wife he's been cheating on. And when yet another affair is discovered, all three women team up to plot mutual revenge on the three-timing SOB.

  19. 19Little Italy

    Little Italy (2018)

    ★ 6.6/10Also comedy and romance

    Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?

  20. 20People We Meet on Vacation

    People We Meet on Vacation (2026)

    ★ 6.9/10Also comedy and romance

    Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.

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