Movies Similar to Once Upon a Winter's Date

Sweet November(2001)

Nelson is a man devoted to his advertising career in San Francisco. One day, while taking a driving test at the DMV, he meets Sara. She is very different from the other women in his life. Nelson causes her to miss out on taking the test and later that day she tracks him down. One thing leads to another and Nelson ends up living with her through a November that will change his life forever.

6.9

A Dash of Love(2017)

A young woman who dreams of opening her own restaurant lands a job at a prominent restaurant whose head chef becomes her unlikely ally when the restaurant's unscrupulous owner, a Master Chef herself, plots to return the place to its former glory by presenting her new assistant's recipes as her own.

6.2

When Harry Met Sally...(1989)

During their travel from Chicago to New York, Harry and Sally debate whether or not sex ruins a friendship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

7.4

Bad Cupid(2021)

Archie is a God on a mission to ensure that true love always wins. Or, short of that, that someone is going to die trying. Not that he particularly cares which outcome it is. That's Archie's "Bad Cupid" approach to romance and beware anyone who gets in his way, especially anyone he's actually trying to help.

4.8

Sleepless in Seattle(1993)

After the death of his mother, a young boy calls a radio station in an attempt to set his father up on a date. Talking about his father’s loneliness soon leads to a meeting with a young female journalist, who has flown to Seattle to write a story about the boy and his father.

6.7

The Notebook(2004)

An epic love story centered around an older man who reads aloud to a woman with Alzheimer's. From a faded notebook, the old man's words bring to life the story about a couple who is separated by World War II, and is then passionately reunited, seven years later, after they have taken different paths.

7.9

Love on Repeat(2019)

Recently split from the "perfect boyfriend," Amber is floundering, her on the job performance uninspired. When Amber starts re-living the same day over and over again, she realizes she is stuck in limbo and must finally decide what it will take to make her truly happy.

4.5

A Walk to Remember(2002)

When the popular, restless Landon Carter is forced to participate in the school drama production, he falls in love with Jamie Sullivan, the daughter of the town's minister. Jamie has a "to-do" list for her life, as well as a very big secret she must keep from Landon.

7.8

Nickelodeon's Not So Valentine's Special(2017)

Nick Stars with the help of Santa Claus and others save Valentine's day from a villainous Cupid.

7.4

Round and Round(2023)

While Rachel is stuck in a time loop, reliving the night of her parents' Hanukkah party, she leans on the boy her grandmother is trying to set her up with to make it out.

6.8

Me Before You(2016)

A small town girl is caught between dead-end jobs. A high-profile, successful man becomes wheelchair bound following an accident. The man decides his life is not worth living until the girl is hired for six months to be his new caretaker. Worlds apart and trapped together by circumstance, the two get off to a rocky start. But the girl becomes determined to prove to the man that life is worth living and as they embark on a series of adventures together, each finds their world changing in ways neither of them could begin to imagine.

7.9

Some Like It Hot(1959)

Two musicians witness a mob hit and struggle to find a way out of the city before they are found by the gangsters. Their only opportunity is to join an all-girl band as they leave on a tour. To make their getaway they must first disguise themselves as women, then keep their identities secret and deal with the problems this brings - such as an attractive bandmate and a very determined suitor.

8.1

Pretty Woman(1990)

While on a business trip in Los Angeles, Edward Lewis, a millionaire entrepreneur who makes a living buying and breaking up companies, picks up a prostitute, Vivian, while asking for directions; after, Edward hires Vivian to stay with him for the weekend to accompany him to a few social events, and the two get closer only to discover there are significant hurdles to overcome as they try to bridge the gap between their very different worlds.

7.5

Groundhog Day(1993)

A narcissistic TV weatherman, along with his attractive-but-distant producer, and his mawkish cameraman, is sent to report on Groundhog Day in the small town of Punxsutawney, where he finds himself repeating the same day over and over.

7.6

Love Actually(2003)

Eight very different couples deal with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London.

7.1

Notting Hill(1999)

London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.

7.3

10 Things I Hate About You(1999)

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.

7.6

It Happened One Valentine's(2017)

When ambitious reporter Allie Rusch is recruited by vindictive music manager Vivian Cartwright to play cupid to famous pop musicians Caleb Greene and Carson Peet in return for an exclusive story over Valentine's weekend, Allie soon realizes Caleb has his sights set on her. Now, torn between her big career move and her growing feelings for Caleb, Allie is left to question whether she can coerce Caleb into something his heart does not desire, or if she should fall in love and make him her very own Valentine.

5.8

The Ugly Truth(2009)

A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.

6.5

Happy Accidents(2000)

A comedy that pays tribute to the science fiction genre -- specifically, the sub-genre of time travel. But here the alternate reality is contemporary New York City where past and future experiences of trust, commitment and denial are cleverly put to the test. Just as Ruby is beginning to relish her first-ever healthy relationship, Sam begins muttering about being a time traveler from the year 2470.

6.8