Movies like The Pain of Love (1989)
The best movies like The Pain of Love (1989) are The Matchmaker's Playbook (2018), All of My Heart: The Wedding (2018) and Holiday Date (2019). If The Pain of Love hooked you with its romance, these 20 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
- NewestGabriel's Rapture: Part I (2021)Released 2021
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 thisAll of My Heart: The Wedding (2018)
Brian and Jenny are planning their wedding at the Inn where they fell in love. When a distant relative arrives and stakes their claim to the Inn, Brian and Jenny must find a way to save their beloved Inn or risk having to sell.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies 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 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 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 thisSailing Into Love (2019)
A biology teacher’s crusade to save a nearby island from development leads to unexpected romance with the handsome and mysterious young sea captain who is new to the seaside town of Willow Bay.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisNostalgic Christmas (2019)
When Anne helps her father close the family's toy store, what she finds will help inspire an entire town that is need of some Christmas cheer.
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 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 thisMy One & Only (2019)
Contestants on the popular reality dating TV show "The One" try to determine if they're fated to be together. Meanwhile, sparks fly between the female contestant and the handsome ranch owner who acts as their guide.
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 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 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 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 thisTurkey Drop (2019)
Lucy Jacobs, a freshman university student, returns home to her small town for Thanksgiving break and suspects she's about to get turkey dropped— aka dumped by her high school sweetheart. To avoid a Turkey Day travesty, Lucy gets out of her comfort zone, proving she's not the same play-it-safe girl she once was.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisTaking a Shot at Love (2021)
Former professional ballet dancer Jenna works with NHL star Ryan Cooper to help him recover from an injury using ballet as therapy, and as they grow close, he helps her mend her injured heart. But when it’s time for Ryan to return to the ice and leave Jenna and her small, Connecticut town, they both must consider the paths they want to take and just maybe, love will find its way.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisDebbie Macomber's Dashing Through The Snow (2015)
Stranded at an airport at Christmastime, Ashley Harrison accepts a ride from Dash Sutherland, who has just rented the last car in town. As the pair heads north, their adventures include car trouble, adopting a puppy and being secretly tailed by federal agents, who believe Ashley is up to no good. With a hint of romance gradually filling the air will these two fall in love or will their journey bring about an unexpected road bump to romance?
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 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 thisEnchanted Christmas (2017)
Weeks before Christmas, interior designer Laura is sent to her hometown of Santa Fe, New Mexico to remodel a landmark hotel. As Laura is kept busy with the renovations, her 8-year-old daughter Nicole is introduced to the art of salsa dancing at a local dance studio. Laura is surprised to find that the studio’s owner is Ricardo, her old high school sweetheart and former salsa dance partner. When Laura and Ricardo reconnect, sparks fly on and off the dance floor. The beautiful Christmas traditions of New Mexico become the backdrop for spirited dancing and unexpected romance.
Why it matches: Recommended by TMDB viewers · both romance
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Frequently asked questions
What are the best movies like The Pain of Love?
The closest matches to The Pain of Love are The Matchmaker's Playbook (2018), All of My Heart: The Wedding (2018) and Holiday Date (2019). Below are 17 more, each with the reason it matches.
What should I watch after The Pain of Love?
Start with The Matchmaker's Playbook (2018), the closest match to The Pain of Love.
What is the highest-rated movie like The Pain of Love?
Gabriel's Rapture: Part I (2021), rated 7.8/10 by 200 TMDB users.
What is the newest movie like The Pain of Love?
Gabriel's Rapture: Part I (2021) is the most recent release on this list.
How are movies similar to The Pain of Love chosen?
First come films that Trakt’s viewers watch alongside The Pain of Love, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.