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Movies like How Not to Propose (2015)

The best movies like How Not to Propose (2015) are Holiday Date (2019), Love in the Sun (2019) and Sailing Into Love (2019). If How Not to Propose hooked you with its romance and tv movie, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Holiday 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 this
  2. Love in the Sun (2019)

    When successful dating app creator Alana hesitantly gets engaged, she returns to her hometown in Florida to deliver the news to her dad. Upon returning home, she crosses paths with her former flame, Kai, and finds herself falling in love with the fun and adventurous lifestyle tied to her community. As Alana and Kai work together to help her dad restore his declining property, Alana finds herself conflicted as to whether or not her current way of living makes her happier than the home and community that she always knew and loved.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  3. Sailing 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 this
  4. All 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 this
  5. Love 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 this
  6. Secret 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 this
  7. Turkey 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 this
  8. Grounded for Christmas (2019)

    When a winter storm hits Cleveland and grounds flights, the nearby hotels quickly fill up with stranded travelers. Nina, a pilot, reluctantly agrees to let her arrogant but charming fellow pilot, Brady, stay at her nearby parents' home. But when they discover her family is hosting a tree trimming party that night and that her ex will be there, Brady pretends to be her boyfriend to help her out.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  9. Marry 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 this
  10. Rome in Love (2019)

    An unknown actress lands the role of a lifetime in Rome. Paired with an American journalist writing a profile, she will discover surprises about love and life in the eternal city.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  11. Valentine in the Vineyard (2019)

    As partners in life and professional winemaking, Frankie Baldwin and Nate DeLuca have different personality types and styles. They’ve just gotten engaged when Frankie’s cousin Lexi and Nate’s brother Marco spring the news that they are getting married – and on Valentine’s Day. Agreeing to keep their plans a secret, Frankie and Nate offer to host Lexi and Marco’s big day.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  12. Matching Hearts (2020)

    As Valentine's Day nears, a matchmaker is tasked by her mentor to find a match for an entrepreneur who believes staying single is the key to success.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  13. Chateau 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 this
  14. A 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 this
  15. Sisters of the Groom (2017)

    When Sarah needs to impress a corporate bigwig in order to help her sister's catering business, she finds herself agreeing to be his son’s pretend date to a family wedding

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  16. Enchanted 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 this
  17. Love and Sunshine (2019)

    Ally Craig has been fostering retired military dog, Sunshine, as she recovers from a broken engagement. But sparks fly again when Sunshine's military partner, Jake Terry, returns to claim the dog.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  18. A 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 this
  19. Christmas 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 this
  20. Christmas 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 this
  21. Ocean Waves (1993)

    At Kichijōji Station, Tokyo, Taku Morisaki glimpses a familiar woman on the platform opposite boarding a train. Later, her photo falls from a shelf as he exits his apartment before flying to Kōchi Prefecture. Picking it up, he looks at it briefly before leaving. As the aeroplane takes off, he narrates the events that brought her into his life...

    Why it matches: Similar story and style · both romance

    Popcorn FlickMovies like this
  22. The Last Night (2019)

    A young couple's last hours together before a trip that will separate them.

    Why it matches: Similar story and style · both romance

  23. Road to Your Heart (2014)

    Basson has five days to make it to his father's funeral in Cape Town, but needs to complete certain tasks on this trip before he can call the family company his own. On the road he meets free-spirited bohemian girl, Amory. As they journey across the breathtaking landscape of South Africa, they meet wonderful characters that allow for hilarious moments and life-changing experiences. Their trip takes a sudden turn for the worst when a villainous figure makes an appearance. Basson and Amory are faced with disappointment and heartache. On the road called life, it is inevitable that you will take some wrong turns. But no matter how hard the road might be, on route to true love is where you will find your true north.

    Why it matches: Similar story and style · both romance

  24. Threesome (2014)

    Som, an ordinary young woman who works as a movie make-up artist. Her longtime live-in boyfriend Rang is also in the business. But the handsome musclebound prop guy – always wearing tight, biceps-baring vest T-shirts – captures many adoring eyes, like that slutty actress, but also his straight-acting gay boss and just about anyone else with a pulse.

    Why it matches: Similar story and style · both romance

  25. Card Zero (2023)

    Before disappearing in the Mojave Desert, Robbie Zagorac captured love, life and heartbreak in a video diary.

    Why it matches: Similar story and style · both romance

  26. Newsies (2017)

    A week in the life of the exploited, child newspaper sellers in turn-of-the-century New York. When their publisher, Joseph Pulitzer, tries to squeeze a little more profit out of their labours, they organize a strike, only to be confronted with the Pulitzer's hard-ball tactics.

    Why it matches: Similar story and style · both romance

    Absolute CinemaMovies like this
  27. A Lady In Waiting (2024)

    A young woman in 1810s England must hide her secret relationship with her maid from her fiancé.

    Why it matches: Similar story and style · both romance

  28. If Lucy Fell (1996)

    Joe and Lucy are roommates and best friends. Lucy, whose love life is embarrassingly dull, convinces Joe, who is infatuated with a neighbor he's never met, that if they don't have stable romances within a month, they must jump off the Brooklyn Bridge.

    Why it matches: Similar story and style · both romance

  29. Natchathiram Nagargiradhu (2022)

    Love and politics collide when modern day individuals working as theatre artists in fall in love while making a play about love. They realize that it's the social structure that determines their values and thoughts, and for their love to succeed, they have to go against it.

    Why it matches: Similar story and style · both romance

  30. The Scent of Green Papaya (1993)

    1950s Saigon through the eyes of Mui, a Vietnamese servant girl. At 10 years-old, Mui leaves her village to work for an affluent, troubled family. As she comes of age, Mui finds work in the household of a pianist she has admired since childhood, and finds their relationship growing in complexity.

    Why it matches: Similar story and style · both romance

    Worth the HypeMovies like this

Like How Not to Propose and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like How Not to Propose?

The closest matches to How Not to Propose are Holiday Date (2019), Love in the Sun (2019) and Sailing Into Love (2019). Below are 27 more, each with the reason it matches.

What should I watch after How Not to Propose?

Start with Holiday Date (2019), the closest match to How Not to Propose.

What is the highest-rated movie like How Not to Propose?

The Scent of Green Papaya (1993), rated 7.0/10 by 223 TMDB users.

What is the newest movie like How Not to Propose?

A Lady In Waiting (2024) is the most recent release on this list.

Are there English movies like How Not to Propose?

Yes: Holiday Date (2019), Love in the Sun (2019) and Sailing Into Love (2019).

How are movies similar to How Not to Propose chosen?

First come films that Trakt’s viewers watch alongside How Not to Propose, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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