Movies like Wind in My Sails (2002)
The best movies like Wind in My Sails (2002) are The Matchmaker's Playbook (2018), Holiday Date (2019) and Attraction (2001). If Wind in My Sails 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 III (2022)Released 2022
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 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 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 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 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 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 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 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 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 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 thisLove in the Forecast (2020)
After swearing off dating for a full year, Leah quickly learns her new commitment has made her a magnet for men.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies 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 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 thisFrequencies (2013)
The story of the forbidden relationship between a 'low born' boy and a 'high born' girl in an alternate reality where every person's relationships and life worth are determined by their innate 'frequencies'.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies 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 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 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 Made to Order (2018)
When architect and Christmas amateur Steven finds himself hosting his family for Christmas, he recruits holiday coordinator Gretchen to bring holiday joy to his home. Gretchen’s expert Christmas spirit brings Steven’s family together, but neither expected it to bring them closer to each other. After a great opportunity presents itself to Gretchen, she and Steven must decide what’s really important in life.
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 thisLove by the Book (2015)
Bookstore owner Emma believes in fairy tales. Although she has yet to be swept away by prince charming, she sees real knight in shining armor potential with a new suitor, Landon. As Emma balances time with Landon and saving her bookstore with once irritating business consultant, Eric, however, she weighs storybook romance against genuine commitment. While she sorts out her feelings toward Landon and Eric, as well as toward love and romance, Emma begins to realize that fairytale endings aren't always by the book.
Why it matches: Recommended by TMDB viewers · both romance
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Frequently asked questions
What are the best movies like Wind in My Sails?
The closest matches to Wind in My Sails are The Matchmaker's Playbook (2018), Holiday Date (2019) and Attraction (2001). Below are 17 more, each with the reason it matches.
What should I watch after Wind in My Sails?
Start with The Matchmaker's Playbook (2018), the closest match to Wind in My Sails.
What is the highest-rated movie like Wind in My Sails?
Gabriel's Rapture: Part I (2021), rated 7.8/10 by 200 TMDB users.
What is the newest movie like Wind in My Sails?
Gabriel's Rapture: Part III (2022) is the most recent release on this list.
Are there English movies like Wind in My Sails?
Yes: The Matchmaker's Playbook (2018), Holiday Date (2019) and Attraction (2001).
How are movies similar to Wind in My Sails chosen?
First come films that Trakt’s viewers watch alongside Wind in My Sails, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.