Movies like 20 Dates (1998)
The best movies like 20 Dates (1998) are A Nice Girl Like You (2020), Play It Again, Sam (1972) and French Girl (2024). If 20 Dates hooked you with its romance and comedy, 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
- NewestThe Love Hypothesis (2026)Released 2026
A Nice Girl Like You (2020)
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisPlay It Again, Sam (1972)
A neurotic film critic obsessed with the movie Casablanca attempts to get over his wife leaving him by dating again with the help of a married couple and his illusory idol, Humphrey Bogart.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisFrench Girl (2024)
Sweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an executive chef position in her hometown of Quebec City. To Gordon’s dismay her future boss also happens to be her former lover, a celebrity Chef with oceanic eyes and a hit TV show. Good luck Gordon.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies 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 thisThe Mating Habits of the Earthbound Human (1999)
David Hyde Pierce, playing an alien (credited as infinity-cubed in the opening credits), narrates a courtship in a late-20th century American city as an extraterrestrial nature documentary. The relationship "footage" is played straight, while the voice-over (with its most often wildly inaccurate theories) and elaborate visual metaphors add comedy.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Love Hypothesis (2026)
Olive Smith, a biology PhD candidate, and Dr. Adam Carlsen, a hotshot professor and well-known tyrant, enter into a fake relationship, seeing each of their carefully calculated theories on love get thrown into chaos.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Absolute CinemaMovies like thisPuppy Love (2023)
After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies 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 List (2023)
After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with someone from hers.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies 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 thisMr. Jealousy (1998)
After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies 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 thisBros (2022)
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPlayers (2024)
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe 4:30 Movie (2024)
In the summer of 1986, three sixteen year old friends spend their Saturdays sneaking into movies at the local multiplex. But when one of the guys also invites the girl of his dreams to see the latest comedy, each of the teens learn more about life and love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisLong Weekend (2021)
Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chance for a fresh start.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisPlaying It Cool (2014)
A young man meets and instantly falls in love with an engaged woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like this7 Days in Hell (2015)
A fictional documentary-style expose on the rivalry between two tennis stars who battled it out in a 1999 match that lasted seven days.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTour de Pharmacy (2017)
A mockumentary that chronicles the prevalence of doping in the world of professional cycling.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHow High (2001)
Jamal and Silas, two ordinary guys who smoke something magical, pass their college entrance exams with flying colors and end up at Harvard. Ivy League ways are strange but Silas and Jamal take it in a stride -- until their supply of supernatural smoke runs dry. That's when they have to start living by their wits and rely on their natural resources to make the grade.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisConfetti (2006)
A mockumentary that follows three couples as they battle it out to win the coveted title of 'Most Original Wedding of the Year'.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisR65: The Silver Generation (2007)
This work is a mockumentary about the love for the silver generation.
Why it matches: Similar story and style · both comedy
12 Pound Balls (2017)
It takes BALLS to win. At least that's what the local bowling clubs in idyllic Warroad, Minnesota used to say, before Emily came along. Now that she has returned to resurrect her name on the champion's board, Gunnar and the boys in town are polishing up their equipment for another shot at the title. This screwball ensemble mockumentary captures Emily's return from retirement, to avenge her loss to Gunnar, and bring justice to her family name. It's gutter-ball madness where split happens.
Why it matches: Similar story and style · both comedy
SEAMUS. Now, Then and Before (2024)
An intertwining story of coincidence and closure. Now, then and before the "death" of his YouTube partner and best friend, Seamus tries to come to terms with his new predicament and create a final video for the channel, a sendoff to the last five years of friendship.
Why it matches: Similar story and style · both comedy
Bad Company (2002)
When a Harvard-educated CIA agent is killed during an operation, the secret agency recruits his twin brother.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisThe Sad Girls of the Mountains (2019)
Four depressed girls in a mountain hideout transform their misery into porn films. The arrival of two gonzo reporters threatens to upset the fragile balance of this feminist micro-utopia.
Why it matches: Similar story and style · both comedy
America's Most Haunted (2013)
The crew of a popular ghost hunting show gets more than they bargained for when they come across a location that's actually haunted.
Why it matches: Similar story and style · both comedy
Drop Dead Gorgeous (1999)
In a small Minnesota town, the annual beauty pageant is being covered by a TV crew. Former winner Gladys Leeman wants to make sure her daughter follows in her footsteps; explosions, falling lights, and trailer fires prove that. As the Leemans are the richest family in town, the police are pretty relaxed about it all. Despite everything, main rival (but sweet) Amber Atkins won't give up without a fight.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisShadowlands (1993)
C.S. Lewis, a world-renowned writer and professor, leads a passionless life until he meets spirited poet Joy Gresham.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisThe Hair Witch Project (1999)
Find out the truth about the terrible fate of three documentary filmmakers who journeyed deep into the woods in search of the legendary Hair Witch... and never came back. One week later, their footage was found... then lost again. Then somebody found it and bootlegged it on the Internet. Then it got lost again, and then it was found and sold to Hard Copy and then they lost it and we found it.
Why it matches: Similar story and style · both comedy
Like 20 Dates and something else?
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Frequently asked questions
What are the best movies like 20 Dates?
The closest matches to 20 Dates are A Nice Girl Like You (2020), Play It Again, Sam (1972) and French Girl (2024). Below are 27 more, each with the reason it matches.
What should I watch after 20 Dates?
Start with A Nice Girl Like You (2020), the closest match to 20 Dates.
What is the highest-rated movie like 20 Dates?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like 20 Dates?
The Love Hypothesis (2026) is the most recent release on this list.
Are there English movies like 20 Dates?
Yes: A Nice Girl Like You (2020), Play It Again, Sam (1972) and French Girl (2024).
How are movies similar to 20 Dates chosen?
First come films that Trakt’s viewers watch alongside 20 Dates, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.