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Movies Like Kissing a Fool

If you liked Kissing a Fool (1998), a comedy and romance movie directed by Doug Ellin, 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. 1The Wedding Ringer

    The Wedding Ringer (2015)

    ★ 6.5/10Also comedy

    Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO…

  2. 2Broadcast News

    Broadcast News (1987)

    ★ 6.8/10Also comedy and romance

    A high-strung news producer finds herself in a love triangle between a talented but self-doubting reporter and a charming news anchor who embodies the growing trivialization of news that she is determined to fight…

  3. 3Bridesmaids

    Bridesmaids (2011)

    ★ 6.5/10Also comedy and romance

    Annie's life is a mess. But when she finds out her lifetime best friend is engaged, she simply must serve as Lillian's maid of honor. Though lovelorn and broke, Annie bluffs her way through the expensive and bizarre…

  4. 4Plus One

    Plus One (2019)

    ★ 6.8/10Also comedy and romance

    Longtime single friends, Ben and Alice, agree to be each other's respective plus one at every wedding they're invited to, during a busy summer of wedding fever.

  5. 5Vanilla Sky

    Vanilla Sky (2001)

    ★ 6.8/10Also romance

    David Aames has it all: wealth, good looks and gorgeous women on his arm. But just as he begins falling for the warmhearted Sofia, his face is horribly disfigured in a car accident. That's just the beginning of his…

  6. 6A Guy Thing

    A Guy Thing (2003)

    ★ 5.9/10Also comedy and romance

    Paul Morse is a good guy. When his friends throw him a wild bachelor party, he just wants to keep his conscience clean -- which is why he's shocked when he wakes up in bed with a beautiful girl named Becky and can't…

  7. 7Bull Durham

    Bull Durham (1988)

    ★ 6.6/10Also comedy and romance

    Veteran catcher Crash Davis is brought to the minor league Durham Bulls to help their up and coming pitching prospect, "Nuke" Laloosh. Their relationship gets off to a rocky start and is further complicated when…

  8. 8American Wedding

    American Wedding (2003)

    ★ 6.2/10Also comedy and romance

    With high school a distant memory, Jim and Michelle are getting married — and in a hurry, since Jim's grandmother is sick and wants to see him walk down the aisle — prompting Stifler to throw the ultimate bachelor…

  9. 9How to Date Billy Walsh

    How to Date Billy Walsh (2024)

    ★ 6.4/10Also romance and comedy

    Archie has been in love with his best friend Amelia for as long as he can remember. Just when he builds up the courage to declare his feelings, she falls head over heels for Billy Walsh, a new American transfer student.

  10. 10The Wedding Year

    The Wedding Year (2019)

    ★ 5.9/10Also comedy

    A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.

  11. 11Everybody Loves Somebody

    Everybody Loves Somebody (2017)

    ★ 6.5/10Also romance and comedy

    On the surface, Clara Barron seems to have it all: a job as an OB-GYN; a great house in LA; and a loving family. But, the one thing Clara doesn't have figured out is her love life. Pressured by a family wedding in…

  12. 12Bachelor Party

    Bachelor Party (1984)

    ★ 6.3/10Also comedy

    On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.

  13. 13The Man with Two Brains

    The Man with Two Brains (1983)

    ★ 6.2/10Also comedy and romance

    A brain surgeon marries a femme fatale, causing his life to turn upside down. Things go more awry when he falls in love with a talking brain.

  14. 14Playing It Cool

    Playing It Cool (2014)

    ★ 5.9/10Also comedy and romance

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

  15. 15That Awkward Moment

    That Awkward Moment (2014)

    ★ 6.1/10Also comedy and romance

    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…

  16. 16How to Murder Your Wife

    How to Murder Your Wife (1965)

    ★ 6.3/10Also comedy

    Stanley Ford is a successful cartoonist and happily single. That is, until he gets drunk at a friend's bachelor party and impulsively proposes to the beautiful woman who pops out of the cake. Once sober, he regrets the…

  17. 17Why Did I Get Married Too?

    Why Did I Get Married Too? (2010)

    ★ 6.6/10Also comedy and romance

    Four couples reunite for their annual vacation in order to socialize and to spend time analyzing their marriages. Their intimate week in the Bahamas is disrupted by the arrival of an ex-husband determined to win back…

  18. 18The 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.

  19. 19¿Quieres ser mi hijo?

    ¿Quieres ser mi hijo? (2023)

    ★ 8.4/10Also comedy and romance

    Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.

  20. 20You're Cordially Invited

    You're Cordially Invited (2025)

    ★ 5.8/10Also comedy and romance

    When two weddings are accidentally booked on the same day at the same venue, each bridal party is challenged with preserving their family's special moment while making the most of the unanticipated tight quarters. In a…

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