Movies like How Not to Date While Trans (2022)
The best movies like How Not to Date While Trans (2022) are How to Date Billy Walsh (2024), She's Gotta Have It (1986) and The Incredible Jessica James (2017). If How Not to Date While Trans 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
- Highest rated¿Quieres ser mi hijo? (2023)8.4/10 from 378 votes
- NewestYoh! Bestie (2026)Released 2026
How to Date Billy Walsh (2024)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisShe'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
Popcorn FlickMovies like thisThe Incredible Jessica James (2017)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisDean (2016)
A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family home in the wake of his mother's death.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisCrossing Delancey (1988)
Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisTwo Can Play That Game (2001)
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 plans to get her man back by any means necessary.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMy Fake Boyfriend (2022)
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 the real love of his life, and breaking up with his fake boyfriend proves hard to do.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisThe Wrong Paris (2025)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisProm Pact (2023)
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 tutoring basketball all-star Graham, she must re-evaluate whether her dream school is worth the cost of everything she believes in.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisThere's Something About Mary (1998)
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 detective he hired to find her.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisAbout Last Night (2014)
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 navigate the relationship minefields from the bar to the bedroom and are eventually put to the test in the real world.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisYoh! Bestie (2026)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisAll Over the Guy (2001)
A contemporary romantic comedy exploring the unlikely pairing of two 20-somethings thrown together by their respective best friends in hopes of igniting their own romance.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisChasing Papi (2003)
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisHellzapoppin' (1941)
Olsen and Johnson, a pair of stage comedians, try to turn their play into a movie and bring together a young couple in love, while breaking the fourth wall every step of the way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like this¿Quieres ser mi hijo? (2023)
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.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Absolute CinemaMovies like thisGirl on a Bicycle (2013)
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 turns Paolo's life upside down.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisSomeone Like You... (2001)
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 begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSplendor (1999)
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisNotting Hill (1999)
London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.
Why it matches: Similar story and style · both romance & comedy
Worth the HypeMovies like thisBecause I Said So (2007)
In an effort to prevent family history from repeating itself, meddlesome mom Daphne Wilder attempts to set up her youngest daughter, Milly, with Mr. Right. Meanwhile, her other daughters try to keep their mom's good intentions under control.
Why it matches: Similar story and style · both romance & comedy
SnoozefestMovies like thisLove Stalk (2016)
Sharon is a fast-rising PR executive from Singapore, searching for love in Hong Kong, who may have found her dream guy, but as she chases after him online and in person, Sharon quickly finds out the dangers of stalking a secret crush.
Why it matches: Similar story and style · both romance & comedy
Blind Dating (2007)
Danny is a blind man who does not let his impairment get in the way of living his life to the fullest, except when it comes to love. Danny's brother sets him up on a series of blind dates, but all of them go disastrously wrong. Just when Danny is about to give up, he meets Leeza, a nurse who works for Danny's doctor. There is just one catch: Leeza, who is from India, is promised to another man.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisWild 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
Worth the HypeMovies like thisSister Act (1992)
When lively lounge singer Deloris sees her mobster beau commit murder, she is relocated for her protection. Set up in the guise of a nun in a California convent, she proceeds to upend the quiet lives of the resident sisters.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Whole Nine Yards (2000)
After a mobster agrees to cooperate with an FBI investigation in order to stay out of prison, he's relocated by the authorities to a life of suburban anonymity as part of a witness protection program. It's not long before a couple of his new neighbours figure out his true identity and come knocking to see if he'd be up for one more hit—suburban style.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisBad Grandmas (2017)
Four grandmothers accidentally kill a conman and, to cover it up, they get rid of the body. When the conman's partner shows up, things go south.
Why it matches: Similar story and style · both comedy
Connection (2025)
A kidnapped woman will be freed on one condition: She must convince her kidnapper that his life is worth living.
Why it matches: Similar story and style · both comedy
The Funny Man (1992)
After winning a house during a poker game, the new owner invests the place with his family. But they will then get acquainted with the 'Funny Man', a sinister jester who has taken up residence there, and whose sense of humor amuses only him, because particularly vicious and bloody.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like How Not to Date While Trans?
The closest matches to How Not to Date While Trans are How to Date Billy Walsh (2024), She's Gotta Have It (1986) and The Incredible Jessica James (2017). Below are 27 more, each with the reason it matches.
What should I watch after How Not to Date While Trans?
Start with How to Date Billy Walsh (2024), the closest match to How Not to Date While Trans.
What is the highest-rated movie like How Not to Date While Trans?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like How Not to Date While Trans?
Yoh! Bestie (2026) is the most recent release on this list.
Are there English movies like How Not to Date While Trans?
Yes: How to Date Billy Walsh (2024), She's Gotta Have It (1986) and The Incredible Jessica James (2017).
How are movies similar to How Not to Date While Trans chosen?
First come films that Trakt’s viewers watch alongside How Not to Date While Trans, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.