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Movies Like How Not to Date While Trans

If you liked How Not to Date While Trans (2022), a comedy and romance movie directed by Nyala Moon, 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. 1How 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.

  2. 2She's Gotta Have It

    She's Gotta Have It (1986)

    ★ 6.6/10Also comedy and romance

    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"…

  3. 3The Wrong Paris

    The Wrong Paris (2025)

    ★ 6.7/10Also romance and comedy

    Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.

  4. 4The Incredible Jessica James

    The Incredible Jessica James (2017)

    ★ 6.1/10Also romance and comedy

    Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.

  5. 5Prom Pact

    Prom Pact (2023)

    ★ 7.2/10Also comedy and romance

    It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts…

  6. 6There's Something About Mary

    There's Something About Mary (1998)

    ★ 6.6/10Also romance and comedy

    For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy…

  7. 7Yoh! Bestie

    Yoh! Bestie (2026)

    ★ 6.3/10Also 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.

  8. 8My Sassy Girl

    My Sassy Girl (2008)

    ★ 6.8/10Also comedy and romance

    A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

  9. 9¿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.

  10. 10About Last Night

    About Last Night (2014)

    ★ 6/10Also comedy and romance

    Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to…

  11. 11Girl on a Bicycle

    Girl on a Bicycle (2013)

    ★ 5.9/10Also comedy and romance

    Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day…

  12. 12Someone Like You...

    Someone Like You... (2001)

    ★ 6/10Also comedy and romance

    Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…

  13. 13My Fake Boyfriend

    My Fake Boyfriend (2022)

    ★ 5.9/10Also comedy and romance

    A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets…

  14. 14Two Can Play That Game

    Two Can Play That Game (2001)

    ★ 6.5/10Also comedy and romance

    Corporate overachiever and all-around fly chick Shanté Smith thinks she's got the goods to keep her slickster boyfriend Keith, from straying—until he discovers a greener pasture, Shanté's archrival, Conny. Scorned, she…

  15. 15Someone Great

    Someone Great (2019)

    ★ 6.4/10Also comedy and romance

    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…

  16. 16Bros

    Bros (2022)

    ★ 6.6/10Also comedy and romance

    Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.

  17. 17Just One of the Guys

    Just One of the Guys (1985)

    ★ 6.4/10Also comedy and romance

    When Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps…

  18. 18What's Love Got to Do with It?

    What's Love Got to Do with It? (2023)

    ★ 6.1/10Also romance and comedy

    Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.

  19. 19Let's Make Love

    Let's Make Love (1960)

    ★ 6.4/10Also comedy and romance

    When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.

  20. 20The Lonely Guy

    The Lonely Guy (1984)

    ★ 6.2/10Also comedy and romance

    A writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.

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