Movies like Jesse James (2021)
The best movies like Jesse James (2021) are Eating Out 2: Sloppy Seconds (2006), The Matchmaker's Playbook (2018) and Paris, Wine & Romance (2019). If Jesse James 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
- NewestJune and John (2025)Released 2025
Eating Out 2: Sloppy Seconds (2006)
How far would you go to get the person of your dreams? With the help of Gwen and Tiffani, Kyle pretends to be heterosexual in order to land Troy, the new guy (and nude model) who's turning the heads of both men and women. He soon finds himself joining the campus ex-gay support group and nabbing a girlfriend! Kyle's ex-boyfriend Marc is horrified at the plan and decides to pursue the confused Troy with his own tactic -- being his "out" gay self. Who will win Troy first?
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisThe 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 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 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 thisTwinkle All the Way (2019)
To pull off a spectacular Christmas-themed wedding, a wedding planner joins forces with the co-owner of a family-run Christmas decoration and house-lighting company.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisAttraction (2001)
A writer/radio advice show host fails to heed his own advice as he stalks his ex-girlfriend and then becomes involved with an actress friend of hers.
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 thisJune and John (2025)
John leads an ordinary life with a monotonous routine. One day John runs into a woman on the subway who is as beautiful as she is mysterious named June. His encounter with her finally leads him to have a goal in his bumptious life.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Christmas Kiss II (2014)
At a Christmastime event, Jenna shares an impromptu, unforgettable kiss with the dashing billionaire, Cooper Montgomery. Unaware of his intentions and fearful of getting hurt in another relationship, Jenna vows to resist his charms, but begins to realize his affection is real as the two spend more time together.
Why it matches: Recommended by TMDB viewers · both romance
SnoozefestMovies like thisA Glenbrooke Christmas (2020)
As Christmas nears, heiress Jessica Morgan seizes what seems like her last chance to experience a relaxed Christmas and heads off to the small town of Glenbrooke, where she meets a handsome fireman.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas Next Door (2017)
Eric Randall, an author of bachelor lifestyle books, is left in charge of his young niece and nephew for the holidays. Eric turns to his neighbor April, a lover of all things Christmas, for help.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisMy Christmas Inn (2018)
With the holiday season in full swing, Jen Taylor is about to score a big promotion at the San Francisco ad agency where she works. But her life is unexpectedly turned upside down when she inherits a cozy inn in Alaska from her aunt. When she goes to inspect the property and meets handsome town attorney Steve Anderson, she's surprised to find that nothing is what she expected. The small town community is full of fun and festive Christmas traditions and soon, Jen starts wondering if the inn might just be the place she belongs, and if Steve could be the Mr. Right she has been waiting for.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisThe Hot Spot (1990)
Upon arriving to a small town, a drifter quickly gets into trouble with the local authorities — and the local women — after he robs a bank.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies 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 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 thisChristmas Under the Stars (2019)
When Nick is fired from his high-powered investment firm at Christmastime, he takes a job at a Christmas tree lot. There, he meets Julie, an astronomy teacher who’s always looked to the stars for hope. As the Christmas spirit washes over him—and he begins falling for Julie—the once self-centered Nick discovers the joy of helping others.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Christmas Prince: The Royal Baby (2019)
Christmas brings the ultimate gift to Aldovia: a royal baby. But first, Queen Amber must help her family and kingdom by finding a missing peace treaty.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisSecret Millionaire (2018)
When a bored millionaire (Steve Lund) is mistaken for a parking attendant by a beautiful girl (Siobhan Williams) who is protesting against his family’s intention of closing a local park, he uses the misunderstanding to get to know her better.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisTrue Romance (1993)
Clarence marries hooker Alabama, steals cocaine from her pimp, and tries to sell it in Hollywood, while the owners of the coke try to reclaim it.
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 thisToast to You (2014)
According to the buttered-cat paradox, cats always land on their feet while buttered toast always lands buttered side down. But if we put a piece of buttered toast on the back of a cat with the buttered side up, and only one will land, which one will that be? Chen Tzu Chen was stood up by his boyfriend Lei-Wang on their third anniversary. While the wedding day of Lei and Hsu Nai Fang is getting closer, Tzu Chen and Lei’s relationship seems to be more tense. However, Tzu Chen can't take it anymore.
Why it matches: Similar story and style · both romance
The Thing About Harry (2020)
Two high school enemies, uber-jock Harry and out-and-proud Sam, are forced to share a car ride to their Missouri hometown for a friend's engagement party on Valentine's Day. Things take a turn when Sam learns Harry has come out.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisBoys on Film 24: Happy Endings (2024)
Let BOYS ON FILM move, inspire and uplift you with this stunning collection of 11 new gay short films, marking the final physical edition of the series. The 11 short films are: We Collide (2023); Firsts (2022); Sea Sparkles [Noctilucas] (2022); Aloof [מנגד] (2020); The Rev (2021); Prelude [Preludio] (2019); Beautiful Stranger (2021); You Like That (2023); Thursday, Friday, Saturday [Jeudi, vendredi, samedi] (2021); The Unknown Man [L'homme inconnu] (2021); S.A.M. (2020).
Why it matches: Similar story and style · both romance
The Wedding Banquet (1993)
A Taiwanese-American man is happily settled in New York with his American boyfriend. He plans a marriage of convenience to a Chinese woman in order to keep his parents off his back and to get the woman a green card. Chaos follows when his parents arrive in New York for the wedding.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisSomething Like Summer (2017)
Something Like Summer traces the tumultuous relationship of Ben and Tim, secret high school sweethearts who grow over the years into both adulthood enemies and complicated friends.
Why it matches: Similar story and style · both romance
SnoozefestMovies like thisDifferent, Night (2017)
Jong-su is visiting Seo-yeon who had compensated dating with him...
Why it matches: Similar story and style · both romance
Sipping (2015)
Santiago and Jared , two teenagers of opposite personality spend an afternoon together looking for ways to overcome their differences. After an act that begins as a game their senses will find the space to coincide.
Why it matches: Similar story and style · both romance
A Short Film About Kissing (2010)
Ian Marcus, the up-and-coming underwear model and method actor, falls for a local girl during the opening day of the Sundance Festival.
Why it matches: Similar story and style · both romance
Sleepers of the City (2009)
A young man contemplates jumping off a bridge when he meets a beautiful woman who could have been his salvation, had she not been dead for the past seventy-five years.
Why it matches: Similar story and style · both romance
Rain in the Sunshine (2013)
Schoolboy Hinata has a big crush on his classmate Shigure, but is too shy to tell her. On the day Shigure is leaving, Hinata flies off on the wings of a bird chasing after her to tell how he feels!
Why it matches: Similar story and style · both romance
Like Jesse James and something else?
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Frequently asked questions
What are the best movies like Jesse James?
The closest matches to Jesse James are Eating Out 2: Sloppy Seconds (2006), The Matchmaker's Playbook (2018) and Paris, Wine & Romance (2019). Below are 27 more, each with the reason it matches.
What should I watch after Jesse James?
Start with Eating Out 2: Sloppy Seconds (2006), the closest match to Jesse James.
What is the highest-rated movie like Jesse James?
Gabriel's Rapture: Part I (2021), rated 7.8/10 by 200 TMDB users.
What is the newest movie like Jesse James?
June and John (2025) is the most recent release on this list.
Are there English movies like Jesse James?
Yes: Eating Out 2: Sloppy Seconds (2006), The Matchmaker's Playbook (2018) and Paris, Wine & Romance (2019).
How are movies similar to Jesse James chosen?
First come films that Trakt’s viewers watch alongside Jesse James, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.