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Movies Like Sin Takes a Holiday

If you liked Sin Takes a Holiday (1930), a romance and comedy movie directed by Paul L. Stein, 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. 15 to 7

    5 to 7 (2014)

    ★ 7.1/10Also comedy and romance

    A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.

  2. 2Bluebeard's Eighth Wife

    Bluebeard's Eighth Wife (1938)

    ★ 7/10Also comedy and romance

    American multi-millionaire Michael Brandon marries his eighth wife, Nicole, the daughter of a broke French Marquis. But she doesn't want to be only a number in the line of his ex-wives and undertakes her own strategy…

  3. 3High Society

    High Society (1956)

    ★ 6.8/10Also comedy and romance

    With socialite Tracy Lord about to remarry, her ex-husband - with the help of a sympathetic reporter - has 48 hours to convince her that she really still loves him.

  4. 4Gentlemen Prefer Blondes

    Gentlemen Prefer Blondes (1953)

    ★ 7.3/10Also comedy and romance

    Lorelei Lee is a beautiful showgirl engaged to be married to the wealthy Gus Esmond, much to the disapproval of Gus' rich father, Esmond Sr., who thinks that Lorelei is just after his money. When Lorelei goes on a…

  5. 5Sabrina

    Sabrina (1995)

    ★ 6.2/10Also romance and comedy

    After her return from school in Paris, a playboy finally takes notice of his family's chauffeur's daughter Sabrina, who's long had a crush on him, but he questions his more serious brother's motives when he warns…

  6. 6The 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.

  7. 7Out to Sea

    Out to Sea (1997)

    ★ 5.9/10Also comedy and romance

    Care-free Charlie cons his widower brother-in-law Herb into an expenses-paid luxury cruise in search of rich, lonely ladies. The catch is that they are required to be dance hosts! With a tyrannical cruise director, and…

  8. 8Cousins

    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.

  9. 9Wedding 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…

  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 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…

  12. 12Housesitter

    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.

  13. 13For Love or Money

    For Love or Money (1993)

    ★ 6.2/10Also comedy and romance

    New York concierge Doug Ireland wants to go into business for himself and refurbish a hotel on Roosevelt Island, N.Y., but he needs an investor. With a few weeks left before his option on the site runs out, Doug agrees…

  14. 14This Little Love of Mine

    This Little Love of Mine (2021)

    ★ 6.1/10Also romance and comedy

    Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the firm’s biggest client – Chip’s…

  15. 15The Seven Year Itch

    The Seven Year Itch (1955)

    ★ 7/10Also comedy and romance

    When his family goes away for summer vacation, a hitherto faithful publishing executive with an overactive imagination is tempted by an attractive new neighbor.

  16. 16Yoh! 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.

  17. 17Intolerable Cruelty

    Intolerable Cruelty (2003)

    ★ 6/10Also comedy and romance

    A revenge-seeking gold digger marries a womanizing Beverly Hills lawyer with the intention of making a killing in the divorce.

  18. 18That Uncertain Feeling

    That Uncertain Feeling (1941)

    ★ 6.6/10Also comedy and romance

    A happily married woman sees a psychoanalyst and develops doubts about her husband.

  19. 19The Right Kind of Wrong

    The Right Kind of Wrong (2013)

    ★ 5.9/10Also romance and comedy

    A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.

  20. 20Love Is in the Air

    Love Is in the Air (2023)

    ★ 6.2/10Also romance and comedy

    A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.

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