Movies like Winterappell (1998)
The best movies like Winterappell (1998) are The Matchmaker's Playbook (2018), X (2011) and Holiday Date (2019). If Winterappell 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
- NewestYou and Me makes Three (2026)Released 2026
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 thisX (2011)
A veteran call girl and a runaway prostitute witness a murder which sends them on an out-of-control roller coaster ride through the twilight zone of sex-for-sale.
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 thisEating 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 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 thisMarry Me at Christmas (2017)
Organizing a Christmas wedding is a true treat for bridal boutique owner Madeline Krug. She loves the challenge of finding the perfect dress for the bride and orchestrating an exquisite event. What Madeline didn’t expect was to be swept off her feet by the bride’s gorgeous brother, movie star, Jonny Blaze. Jonny came to the quirky town of Fool’s Gold to support his sister -- not to fall in love. Yet Madeline is the most extraordinary woman he’s ever met, and she finds the real Jonny even more captivating than her celebrity crush. Will the action star be brave enough to take on the role of a lifetime?
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas in Evergreen: Tidings of Joy (2019)
A skeptical writer shows up in Evergreen to get the scoop on the town's famed passion for Christmas during a search for a long-lost time capsule.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies 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 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 thisOn the 12th Date of Christmas (2020)
Two seemingly incompatible game designers team up to create a romantic, city-wide scavenger hunt themed for the "12 Days of Christmas."
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies 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 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 thisScaramouche (1952)
In 18th-century France, a young man masquerades as an actor to avenge his friend's murder.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies 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 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 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 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 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 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 thisSharing Christmas (2017)
A real estate developer is given the opportunity of his career to transform an old shopping complex into a prime location. Unfortunately, there is one tenant who is holding out—the Christmas shop owner he met by happenstance just days ago.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Night Like This (2025)
A stone-broke gay actor and a privileged screw-up with a failing business cross paths on a winter night and join forces in a quest around London to find a meaning to their miserable lives, but when their unlikely connection turns into something deeper, fears and demons from their past come to jeopardise the whole mission.
Why it matches: Similar story and style · both romance
You and Me makes Three (2026)
Alannah and Amara are a married couple in their early thirties, finally ready to start a family. After a chaotic kids' birthday party full of unfiltered parenting confessions, their dream of having a child becomes stronger than ever. Their journey through fertility options is funny, messy, and deeply human from anonymous donor apps to their gay best friends, David and Tom, offering to help. What follows is a series of awkward, hilarious attempts at home insemination (yes, with science goggles) and the very real emotional ups and downs of trying to conceive. Each negative test hits hard, but support from Amara's mum, Joy, and the couple's rock-solid partnership keeps them going.
Why it matches: Similar story and style · both romance
Title 18 (2022)
An experimental short film made as part of a multi-media triptych, originally screened alongside a fashion collection and an art-installation. Drawing from Papa Yorick’s (Director and fashion designer) thesis “Men Are My Cumrag”, the film reenacts eight mainstay gay porn scripts, incorporating and parodying tropes and clichés, that explore masculine identities within the gay porn industry, through a satirical and critical lens.
Why it matches: Similar story and style · both romance
The Shedding (2026)
When his lover, a rising actor, leaves him for his own stand-in, Jean spirals into doubt and obsession. Caught between dream and reality, on a chaotic film set where everything is an illusion, he embarks on a troubling quest. Must he reinvent himself to win him back, or risk losing himself entirely?
Why it matches: Similar story and style · both romance
Vin (2026)
Connor Smash, a seventeen-year-old with more questions than answers, receives a letter from his mysterious lover, Vin. The note is short but urgent, asking him to meet at the special place they’ve only ever spoken about in their letters. With no clear clue which spot Vin means, Connor sets out, moving from one meaningful place to another, hoping each stop might finally lead him to Vin.
Why it matches: Similar story and style · both romance
Antique (2008)
Jin-hyeok opens a cake shop in an old antique shop, hiring Seon-woo, Korea's best pastry chef, who fell in love with him in high school. Also there are Soo-yeong, crushing on Seon-woo, ex-boxer Ki-beom, and Seon-woo's French ex-boyfriend.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisKnife+Heart (2018)
In the summer of 1979, gay porn producer Anne sets out to film her most ambitious film yet, but her actors are picked off, one by one, by a mysterious killer.
Why it matches: Similar story and style · both romance
SnoozefestMovies like thisFetish in E(x)ile (2025)
They met onstage at the Mr Leather Russia contest. One of them won the title, the other won the titleholder. 'A tale of two Doms', gay fetish and BDSM activists who tried to make a difference. But soon their world came crashing down.
Why it matches: Similar story and style · both romance
Soma Ulte (TBA)
Openly gay and privately on the autism spectrum, 19-year-old Aidan tries to win over the heart of his bisexual best friend, Blake, despite his constant struggles with social interactions.
Why it matches: Similar story and style · both romance
No Me Mires Así (TBA)
The intimacy between Manuel and Fermín begins to crack when Fermín starts a new job and the pressure to fit in reawakens old fears. Outside, hateful rhetoric begins to echo again; inside, their love is confronted with uncertainty.
Why it matches: Similar story and style · both romance
Like Winterappell and something else?
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Frequently asked questions
What are the best movies like Winterappell?
The closest matches to Winterappell are The Matchmaker's Playbook (2018), X (2011) and Holiday Date (2019). Below are 27 more, each with the reason it matches.
What should I watch after Winterappell?
Start with The Matchmaker's Playbook (2018), the closest match to Winterappell.
What is the highest-rated movie like Winterappell?
Gabriel's Rapture: Part I (2021), rated 7.8/10 by 200 TMDB users.
What is the newest movie like Winterappell?
You and Me makes Three (2026) is the most recent release on this list.
Are there English movies like Winterappell?
Yes: The Matchmaker's Playbook (2018), X (2011) and Holiday Date (2019).
How are movies similar to Winterappell chosen?
First come films that Trakt’s viewers watch alongside Winterappell, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.