Movies Most Similar to One Winter Proposal (2019)

Movies like One Winter Proposal (2019).

23 items, 700 votes
Movies Most Similar to One Winter Proposal (2019)
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Tramps (2016)

Tramps (2016) - Movies Most Similar to One Winter Proposal (2019)
Starring: Callum Turner, Grace Van Patten, Michal Vondel, Mike Birbiglia
Duration: 1h 22mins
Genres: Comedy, Romance

Tramps is a 2016 American comedy film directed by Adam Leon and starring Callum Turner and Grace Van Patten.
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To All the Boys: P.S. I Still Love You (2020)

To All the Boys: P.S. I Still Love You (2020) - Movies Most Similar to One Winter Proposal (2019)
Starring: Lana Condor, Noah Centineo, Jordan Fisher, Anna Cathcart
Duration: 1h 41mins
Genres: Comedy, Drama, Romance

Lara Jean Covey's (Lana Condor) high school sets up a volunteer program; while her boyfriend Peter Kavinsky (Noah Centineo) volunteers with his friends, Lara Jean goes to Belleview Retirement Home instead, where her older sister Margot (Janel Parrish) went.
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Love, Rosie (2014)

Love, Rosie (2014) - Movies Most Similar to One Winter Proposal (2019)
Starring: Lily Collins, Sam Claflin, Christian Cooke, Jaime Winstone
Duration: 1h 42mins
Genres: Comedy, Romance

Alex and Rosie have been best friends for almost as long as they can remember.
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The Romantics (2010)

The Romantics (2010) - Movies Most Similar to One Winter Proposal (2019)
Starring: Katie Holmes, Anna Paquin, Josh Duhamel, Malin Akerman
Duration: 1h 35mins
Genres: Comedy, Drama, Romance

A group of seven college friends, who called themselves The Romantics (because of a shared interest in the Romantic Era), reunite after six years when two of them, Lila and Tom, are planning to marry.
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With This Ring (2015)

With This Ring (2015) - Movies Most Similar to One Winter Proposal (2019)
Starring: Regina Hall, Jill Scott, Eve, Brooklyn Sudano
Duration: 1h 27mins
Genres: Comedy, Romance

Trista, a career-driven talent agent, has not gotten over her commitment-phobic ex; gossip columnist Viviane is still in love with the father of her son; and struggling actress Amaya will do anything to sabotage the marriage of her boyfriend.
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Serendipity (2001)

Serendipity (2001) - Movies Most Similar to One Winter Proposal (2019)
Starring: John Cusack, Kate Beckinsale, Jeremy Piven, Bridget Moynahan
Duration: 1h 30mins
Genres: Comedy, Romance

During the Christmas season in New York City, Jonathan Trager encounters Sara Thomas at Bloomingdale's while they attempt to buy the same pair of black cashmere gloves.
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My Little Monster (2018)

My Little Monster (2018) - Movies Most Similar to One Winter Proposal (2019)
Starring: Masaki Suda, Tao Tsuchiya, Yûki Furukawa, Minami Hamabe
Duration: 1h 45mins
Genres: Comedy, Drama, Romance

My Little Monster focuses on the relationship between Shizuku Mizutani, who has absolutely no interests except in studying and her plans for the future, and a boy named Haru Yoshida, who sits next to Shizuku in class but rarely attends school.
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The Opposite Sex and How to Live with Them (1992)

The Opposite Sex and How to Live with Them (1992) - Movies Most Similar to One Winter Proposal (2019)
Genres: Comedy, Romance

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Dreamfactory (2019)

Dreamfactory (2019) - Movies Most Similar to One Winter Proposal (2019)
Starring: Emilia Schüle, Ken Duken, Svenja Jung, Anatole Taubman
Duration: 2h 5mins
Genres: Comedy, Drama, Romance

A romantic drama set in 1961 that follows a young studio extra's ambitious efforts to reunite with the French girl he loves after being separated by the construction of the Berlin Wall.
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Bed & Breakfast: Love Is a Happy Accident (2010)

Bed & Breakfast: Love Is a Happy Accident (2010) - Movies Most Similar to One Winter Proposal (2019)
Starring: Dean Cain, Juliana Paes, Bill Engvall, Julian Stone
Duration: 1h 29mins
Genres: Comedy, Romance

Bed & Breakfast is a 2010 romantic comedy directed by Márcio Garcia and written by Leland Douglas. Produced by B. B. Film Productions and F. J.
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Kiss the Bride (2007)

Kiss the Bride (2007) - Movies Most Similar to One Winter Proposal (2019)
Starring: Tori Spelling, Philipp Karner, James O'Shea, Joanna Cassidy
Duration: 1h 40mins
Genres: Comedy, Romance

Matt (Philipp Karner) and Ryan (James O'Shea) were best friends in high school, but ten years later, Matt receives an invitation to Ryan's wedding, he is surprised - especially that Ryan's intended, whose name is Alex, is a woman (Tori Spelling).
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Love and Sunshine (2019)

Love and Sunshine (2019) - Movies Most Similar to One Winter Proposal (2019)
Starring: Danica McKellar, Mark Deklin, Christine Chatelain, Peter Benson
Duration: 1h 24mins
Genres: Romance

A woman has been fostering a dog as she recovers from a broken heart. As the owner returns to claim the dog will sparks fly or will it just lead to another broken heart?.
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The Holiday (2006)

The Holiday (2006) - Movies Most Similar to One Winter Proposal (2019)
Starring: Kate Winslet, Cameron Diaz, Jude Law, Jack Black
Duration: 2h 16mins
Genres: Comedy, Romance

Iris Simpkins, a society columnist for The Daily Telegraph in London, still loves her ex-boyfriend, Jasper Bloom, despite the fact that he cheated on her and is emotionally needy.
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A Faithful Man (2018)

A Faithful Man (2018) - Movies Most Similar to One Winter Proposal (2019)
Starring: Louis Garrel, Laetitia Casta, Lily-Rose Depp, Joseph Engel
Duration: 1h 15mins
Genres: Comedy, Drama, Romance

A Faithful Man (French: L'Homme fidèle) is a 2018 French romantic comedy-drama film directed by Louis Garrel, from a screenplay by Garrel and Jean-Claude Carrière.
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Destination Wedding (2017)

Destination Wedding (2017) - Movies Most Similar to One Winter Proposal (2019)
Starring: Alexa PenaVega, Jeremy Guilbaut, Rafael Simón, Andrea Brooks
Duration: 1h 24mins
Genres: Comedy, Romance

Frank and Lindsay meet at the airport as they wait to board their flight to Paso Robles. As they talk, they realize that they are both in town for the same wedding.
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Little Italy (2018)

Little Italy (2018) - Movies Most Similar to One Winter Proposal (2019)
Starring: Emma Roberts, Hayden Christensen, Danny Aiello, Andrea Martin
Duration: 1h 42mins
Genres: Comedy, Romance

Nikki and Leo both grow up in Toronto's Little Italy neighborhood, where their families are running a pizza business together.
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Ali's Wedding (2017)

Ali's Wedding (2017) - Movies Most Similar to One Winter Proposal (2019)
Starring: Osamah Sami, Don Hany, Helana Sawires, Robert Rabiah
Duration: 1h 50mins
Genres: Comedy, Drama, Romance

Ali (Osamah Sami), the charming and musically-talented son of a Muslim cleric (Don Hany), struggles to make the right life choices despite the best of intentions.
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Bad Date Chronicles (2017)

Bad Date Chronicles (2017) - Movies Most Similar to One Winter Proposal (2019)
Starring: Merritt Patterson, Justin Kelly, Lanie McAuley, Giles Panton
Duration: 1h 24mins
Genres: Comedy, Romance

Leigh runs the website "Bad Date Chronicles," which allows people to anonymously post horrible date experiences.
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Sun, Sand & Romance (2017)

Sun, Sand & Romance (2017) - Movies Most Similar to One Winter Proposal (2019)
Starring: Tricia Helfer, Paul Campbell, Scott Elrod, Tim Russ
Duration: 1h 24mins
Genres: Comedy, Family, Romance

Kate (Helfer), a driven accounting executive, heads to Cancun with her boyfriend Eric, an equally ambitious land development executive, for some much-needed rest and relaxation.
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Always Be My Maybe (2019)

Always Be My Maybe (2019) - Movies Most Similar to One Winter Proposal (2019)
Starring: Ali Wong, Randall Park, James Saito, Michelle Buteau
Duration: 1h 41mins
Genres: Comedy, Romance

Sasha Tran and Marcus Kim are childhood friends who grow up next door to each other in San Francisco.
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