Movies like The Woman Of My Life (1966)
The best movies like The Woman Of My Life (1966) are Chasing the Wind (2025), Endless Love (2017) and Holiday Date (2019). If The Woman Of My Life 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
- NewestChasing the Wind (2025)Released 2025
Chasing the Wind (2025)
A focused city worker and a laid-back surfer - both heirs to the same company - find they have plenty in common when they join forces in the boardroom.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisEndless Love (2017)
Sparks fly when a humble housekeeper crosses paths with a wealthy surgeon, but a devastating truth puts their relationship to the test.
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 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 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 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 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 thisFive Star Christmas (2020)
After moving back to her hometown, Lisa (Lenz) plots with her siblings and grandparents to help her father's bed and breakfast get a five-star review from an incognito travel critic (Webster), but ends up falling for him, not knowing he is the real critic.
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 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 thisSense, Sensibility & Snowmen (2019)
Christmas enthusiast party planners Ella and her sister, Marianne, clash with their client, Edward, who is a not-so-jolly toy company CEO.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas On My Mind (2019)
When Lucy wakes up with a wedding dress in hand, she believes that she is late to her wedding with her ex-boyfriend Zac. However, she has no recollection of the past 2 years, including the fact that she is engaged to another man.
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 thisAngel of Christmas (2015)
Susan is a newspaper staffer who decides to generate some Christmas spirit by writing an article about her family’s storied 100-year-old, hand-carved, heirloom Christmas angel. This leads her to accidentally meet Brady, a cute, upbeat artist who insists that he and Susan become fast friends (at least). It turns out that this angel also has the spiritual power to bring people together – as it seems to be doing with Susan and Brady. What’s behind this enchanted ornament? As time moves on, more about this captivating artifact is revealed.
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 thisBrimming with Love (2018)
Allie is an aspiring journalist who meets Sam, a coffee shop owner who plays matchmaker for his customers. Allie agrees to be matched but going though Sam's process causes her to see that her perfect match might just be the matchmaker himself.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies 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
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 thisLast Chance for Christmas (2015)
When Prancer injures his hoof Santa’s stable hand, John, must find a fill in to ensure Christmas deliveries go off without a hitch. His mission gets complicated when he discovers that Frankie, the perfect substitute reindeer, belongs to a precocious 8-year-old girl and her mother Annie. As he races to get Frankie up to the North Pole, he realizes that he’s actually falling in love with Annie and has to find a way to win her over and save Christmas at the same time.
Why it matches: Recommended by TMDB viewers · both romance
SnoozefestMovies like this
Like The Woman Of My Life and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like The Woman Of My Life?
The closest matches to The Woman Of My Life are Chasing the Wind (2025), Endless Love (2017) and Holiday Date (2019). Below are 17 more, each with the reason it matches.
What should I watch after The Woman Of My Life?
Start with Chasing the Wind (2025), the closest match to The Woman Of My Life.
What is the highest-rated movie like The Woman Of My Life?
Gabriel's Rapture: Part I (2021), rated 7.8/10 by 200 TMDB users.
What is the newest movie like The Woman Of My Life?
Chasing the Wind (2025) is the most recent release on this list.
How are movies similar to The Woman Of My Life chosen?
First come films that Trakt’s viewers watch alongside The Woman Of My Life, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.