Movies like Henry's First Dates (2026)
The best movies like Henry's First Dates (2026) are 50 First Dates (2004), Love, Weddings & Other Disasters (2020) and Little Italy (2018). If Henry's First Dates 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 ratedThe Holiday (2006)7.1/10 from 5,835 votes
- NewestThe Brainrotter (2026)Released 2026
50 First Dates (2004)
Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLove, Weddings & Other Disasters (2020)
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLittle Italy (2018)
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
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 thisWhat's Love Got to Do with It? (2023)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisGood Advice (2001)
An investment banker loses everything and must discover what's really important in life.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies 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 thisOverboard (2018)
A spoiled, wealthy yacht owner is thrown overboard and becomes the target of revenge from his mistreated employee.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies 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 thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisRelationship Goals (2026)
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her priorities.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove Is in the Air (2023)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Lonely Guy (1984)
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.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisI Fine..Thank You Love You (2014)
Desperate to go to the U.S. to win back his girlfriend, Yim hires a tutor to teach him English. But things don't go according to plan.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisOnly the Lonely (1991)
Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna, whose father owns the local funeral parlour. Naturally, his mother objects to the relationship, and Danny and Theresa must either overcome her objections or give up the romance.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisBoot Camp (2024)
Unathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self and ignore the others' expectations.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisKiss Me, Stupid (1964)
While traveling home from Vegas, an amorous lounge singer named Dino gets conned by a local mechanic/songwriter into staying in town for the night. The mechanic's songwriting partner, Orville, offers Dino his home for overnight lodging and enlists a local waitress/call girl to pose as his wife in order to placate Dino's urges.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies 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 thisThe Disorderly Orderly (1964)
Poor Jerome Littlefield. He wants to be a doctor – but that's not exactly the perfect career choice when you're hopelessly squeamish. So he settles for the job of orderly at the Whitestone Sanitarium, a career move that's guaranteed to keep the patients – and viewers – in stitches!
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMissão Cupido (2021)
Miguel is Rita's clumsy guardian angel. Unaware of the extent of his powers, he prophesies that the girl will never find love. However, when Death learns of his audacity, he comes to Earth to seduce Rita. Now, by order of the Almighty, Miguel has to face Death and the problems he caused his protégé.
Why it matches: Similar story and style · both comedy & romance
The Holiday (2006)
Two women, one American and one British, swap homes at Christmastime following bad breakups. Each woman finds romance with a local man but realizes that the imminent return home may end the relationship.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisThe Brainrotter (2026)
Why it matches: Similar story and style · both romance & comedy
Playing It Cool (2014)
A young man meets and instantly falls in love with an engaged woman.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisOverboard (1987)
Heiress Joanna Stayton hires carpenter Dean Proffitt to build a closet on her yacht—and refuses to pay him for the project when it's done. But after Joanna accidentally falls overboard and loses her memory, Dean sees an opportunity to get even.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisIn The Form of Love (2023)
Iran in the early 1960s: The world is still a big dream of freedom, exuberance and Technicolor, at least in the eyes of sixteen-year-old Atieh (Saina Rohanie in an impressive debut). Together with her mother, she visits Rassoul, a longtime friend of her late father, in his small village and, upon her arrival, meets his fourteen-year-old son Kamran (new discovery Mahdiar Shahmohammadi). Kamran is immediately enraptured by Atieh's charisma, and it doesn't take long for the two teens to become close. Kamran takes Atieh into the previously unknown world of cinema, whose heroes, villains and adventures he is already passionately addicted to. A magical summer takes its course - at the end of which waits a shattering decision that will change both of them forever.
Why it matches: Similar story and style · both romance
The Lake House (2006)
When architect Alex Wyler moves into an unusual glass house on stilts over a lake, he discovers a note from the previous tenant in the mailbox--but no one's lived in the house for years. He replies and soon discovers that he's corresponding with a doctor named Kate Forster. Their correspondence, only through the 'magical' mailbox, turns romantic and their paths cross in unexpected ways, but when they try to truly connect, danger looms. They must try to unravel the mystery behind their extraordinary romance before it's too late.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisMy Name Is Loh Kiwan (2024)
After defecting from North Korea, Loh Kiwan struggles to obtain refugee status in Belgium, where he encounters a dejected woman who has lost all hope.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisLucid Love (2024)
Juno, an ordinary man, always feels insecure because he has a beautiful girlfriend, while Trish, a beautiful woman, is always played by men. They never expected to meet in a place full of wonders, a place that would determine their love lives, in a lucid dream.
Why it matches: Similar story and style · both romance
Ellipsis (2018)
In the middle of a crowded city the paths of two strangers, a man and a woman, collide. This accidental, chance occurrence sets in motion a chain of events that sees the two strangers embark on a night of adventure and connection that challenges their separate lives.
Why it matches: Similar story and style · both romance
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Frequently asked questions
What are the best movies like Henry's First Dates?
The closest matches to Henry's First Dates are 50 First Dates (2004), Love, Weddings & Other Disasters (2020) and Little Italy (2018). Below are 27 more, each with the reason it matches.
What should I watch after Henry's First Dates?
Start with 50 First Dates (2004), the closest match to Henry's First Dates.
What is the highest-rated movie like Henry's First Dates?
The Holiday (2006), rated 7.1/10 by 5,835 TMDB users.
What is the newest movie like Henry's First Dates?
The Brainrotter (2026) is the most recent release on this list.
How are movies similar to Henry's First Dates chosen?
First come films that Trakt’s viewers watch alongside Henry's First Dates, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.