Movies like How, When, and with Whom (1969)
The best movies like How, When, and with Whom (1969) are The Matchmaker's Playbook (2018), It Was Always You (2021) and Paris, Wine & Romance (2019). If How, When, and with Whom hooked you with its romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedGabriel's Rapture: Part I (2021)7.8/10 from 200 votes
- NewestLa Bohème (2026)Released 2026
- In ItalianThe Laughing Woman (1969)Also in Italian
The Matchmaker's Playbook (2018)
After a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a successful and secretive dating service. But when Blake Olson requests the services of Wingmen, Inc., Ian may have landed his most hopeless client yet. As Blake begins the transformation from hot mess to smokin' hot, Ian realizes he's in danger of breaking his cardinal rule....
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisIt Was Always You (2021)
Elizabeth's engagement plans are thrown into disarray when her fiancée's free-spirited brother David returns home. David's unexpected influence prompts Elizabeth to question her life decisions.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisParis, Wine & Romance (2019)
Isabella is the ambitious new owner of her family’s Oregon winery whose dream of becoming world-renowned takes a big step forward when she enters a prestigious wine competition in Paris. Upon arrival, Isabella meets her biggest competitor, Jacques, from one of the world’s foremost winemaking families. Impressed by Isabella and her expertise in wine, a budding romance develops between them.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisSafe Haven (2013)
A young woman with a mysterious past lands in Southport, North Carolina where her bond with a widower forces her to confront the dark secret that haunts her.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisGabriel's Rapture: Part I (2021)
In the fourth instalment of the Gabriel's Inferno series, Professor Gabriel Emerson has embarked on a passionate, yet clandestine affair with his former student Julia Mitchell, but when they return from their romantic holiday in Italy, their happiness is threatened. Will Gabriel succumb to Dante's fate?
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisA Godwink Christmas: Meant For Love (2019)
Multiple coincidences and a chance meeting bring together Alice and Jack, two strangers from very different family backgrounds, for an unexpected Christmastime courtship filled with personal revelations, misread signals, and a very real health scare that will either destroy or strengthen the budding romance.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisGabriel's Rapture: Part III (2022)
In the sixth installment of the Gabriel's Inferno series, Julia deals with the aftermath of Gabriel's departure, while Gabriel goes on a journey of self-discovery. Will they reunite and be able to repair what is broken?
Why it matches: Recommended by TMDB viewers · both romance
Absolute CinemaMovies like thisA Little Christmas Charm (2020)
Holly, a jewelry designer finds a lost charm bracelet and teams up with investigative reporter Greg in hopes of finding the owner and returning it by Christmas Eve.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Gift to Remember (2017)
After colliding with a pedestrian on her bicycle who loses his memory following the accident, Darcy Archer becomes determined to help the handsome guy figure out who he is. In the process, she finds out a lot more about who she is, what she wants from life, and how this too-good-to-be-true guy might just be the man she’s been waiting to bump into all her life.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisGabriel's Rapture: Part II (2022)
In the fifth installment of the Gabriel's Inferno series, Gabriel and Julia’s happiness is threatened by a conspiring student and academic politics. When Gabriel is confronted by the university administration, will he succumb to Dante's fate? Or will he fight to keep Julia, his Beatrice, forever?
Why it matches: Recommended by TMDB viewers · both romance
Absolute CinemaMovies like thisNot Cinderella's Type (2018)
Indy lives with her aunt and uncle and believes her life is fine until an accident brings a new guy into her life. Bryant Bailey is not Indy's type - she's never been into guys like him. But then again, she's never really known anyone so stubborn and caring that can also help her discover who she is and what she's worth. A modern telling of Cinderella, based on the novel by Jenni James.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisSisters of the Groom (2017)
When Sarah needs to impress a corporate bigwig in order to help her sister's catering business, she finds herself agreeing to be his son’s pretend date to a family wedding
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisRome in Love (2019)
An unknown actress lands the role of a lifetime in Rome. Paired with an American journalist writing a profile, she will discover surprises about love and life in the eternal city.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisHoliday Date (2019)
When Brooke’s boyfriend, Ethan, breaks up with her just before the holidays, she agrees to go home with Joel, an actor who will pose as her boyfriend.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChateau Christmas (2020)
Margot, a world-renowned pianist, returns to Chateau Newhaus to spend the holidays with her family and is reunited with an ex who helps her rediscover her passion for music.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisThe Laughing Woman (1969)
Beautiful PR woman, Maria finds herself trapped in the home of the sinister and troubled Dr. Sayer, where she is subjected to a series of increasingly bizarre, terrifying, and degrading sex games. Sayer admits that he has murdered several women after the same ordeal, always killing them at the point of orgasm. But all is not what it seems, and through a series of twists and turns, the whole situation is slowly turned on its head.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Royal Christmas (2014)
A young working girl with a blue-collar background is surprised when her new fiancé announces he is actually a prince of a small sovereign country in Europe. After the couple quickly takes off to spend the holidays at his family’s sprawling, royal castle, she must work hard to win over her disapproving and unaccepting future mother-in-law—the Queen—and find out if love truly can conquer all.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisValentine in the Vineyard (2019)
As partners in life and professional winemaking, Frankie Baldwin and Nate DeLuca have different personality types and styles. They’ve just gotten engaged when Frankie’s cousin Lexi and Nate’s brother Marco spring the news that they are getting married – and on Valentine’s Day. Agreeing to keep their plans a secret, Frankie and Nate offer to host Lexi and Marco’s big day.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisLove in the Sun (2019)
When successful dating app creator Alana hesitantly gets engaged, she returns to her hometown in Florida to deliver the news to her dad. Upon returning home, she crosses paths with her former flame, Kai, and finds herself falling in love with the fun and adventurous lifestyle tied to her community. As Alana and Kai work together to help her dad restore his declining property, Alana finds herself conflicted as to whether or not her current way of living makes her happier than the home and community that she always knew and loved.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisForever in My Heart (2019)
Jenna and Charlie found love in Ireland but their dreams drove them apart. Five years later, they reunite and Jenna has to decide where her heart belongs—back home or in the Emerald Isle.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisDoctor Zhivago (1965)
The life of a Russian physician and poet who, although married to another, falls in love with a political activist's wife and experiences hardship during World War I and then the October Revolution.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisMilea (2020)
Years after his teen romance with Milea, a now-adult Dilan tells his version of their love story when a high school reunion brings them back together.
Why it matches: Similar story and style · both romance
Notes on a Scandal (2006)
A veteran high school teacher befriends a younger art teacher, who is having an affair with one of her 15-year-old students. However, her intentions with this new "friend" also go well beyond platonic friendship.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisThe Beach (2000)
Twenty-something Richard travels to Thailand and finds himself in possession of a strange map. Rumours state that it leads to a solitary beach paradise, a tropical bliss - excited and intrigued, he sets out to find it.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisBonjour Tristesse (1958)
A spoiled teenager spends the summer at the French Riviera with her rich, widower, playboy father, but when his old flame resurfaces, she resolves to keep her frivolous lifestyle at all costs.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisStardust (2007)
In a countryside town bordering on a magical land, a young man makes a promise to his beloved that he'll retrieve a fallen star by venturing into the magical realm. His journey takes him into a world beyond his wildest dreams and reveals his true identity.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisBicentennial Man (1999)
Richard Martin buys a gift, a new NDR-114 robot. The product is named Andrew by the youngest of the family's children. "Bicentennial Man" follows the life and times of Andrew, a robot purchased as a household appliance programmed to perform menial tasks. As Andrew begins to experience emotions and creative thought, the Martin family soon discovers they don't have an ordinary robot.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisBirds Without Names (2017)
An unstable young woman pines for the ex-boyfriend who nearly beat her to death – and who has mysteriously disappeared.
Why it matches: Similar story and style · both romance
La Bohème (2026)
In present day East End, an aspiring novelist falls in love with a Ukrainian cleaner whilst his best friend attempts to rekindle his romance with a social climbing sex bomb.
Why it matches: Similar story and style · both romance
Ask the Dust (2006)
Mexican beauty Camilla hopes to rise above her station by marrying a wealthy American. That is complicated by meeting Arturo Bandini, a first-generation Italian hoping to land a writing career and a blue-eyed blonde on his arm.
Why it matches: Similar story and style · both romance
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Frequently asked questions
What are the best movies like How, When, and with Whom?
The closest matches to How, When, and with Whom are The Matchmaker's Playbook (2018), It Was Always You (2021) and Paris, Wine & Romance (2019). Below are 27 more, each with the reason it matches.
What should I watch after How, When, and with Whom?
Start with The Matchmaker's Playbook (2018), the closest match to How, When, and with Whom.
What is the highest-rated movie like How, When, and with Whom?
Gabriel's Rapture: Part I (2021), rated 7.8/10 by 200 TMDB users.
What is the newest movie like How, When, and with Whom?
La Bohème (2026) is the most recent release on this list.
Are there Italian movies like How, When, and with Whom?
Yes: The Laughing Woman (1969).
How are movies similar to How, When, and with Whom chosen?
First come films that Trakt’s viewers watch alongside How, When, and with Whom, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.