ULTIMATE LIST OF ROMANTIC WINTER MOVIES

Happy December friends! Welcome to my Ultimate Guide to Romantic Winter Movies!

If there’s nothing you love more in the winter than hunkering down and watching movies full of snow, cheer, romance, and maybe even a little mystery and action – congrats on finding this post, because I wrote it just for you!

This list contains over 50 titles that are perfect for every mood you may experience this winter. Notice how I keep calling them ‘winter‘ movies and not ‘Christmas‘ movies? That’s because unlike most lists, this list contains a huge dose of movies that are not based entirely on Christmas. While it is chock full of classics, it also features a lot of ‘regular’ films set in snowy locales – which means you can keep watching right through January!

Plus, I included who I think each movie pairs well with, to make it even easier for you to choose a flick when you snuggle in.

Enjoy, and Happy Holidays!

TO WATCH WITH YOUR BEST FRIEND…

The Holiday (2006)

Two very different women have one thing in common – being unlucky-in-love. They try ‘house swapping’ for their holiday vacations, with one traveling to England, and the other to L.A. Fun, heartfelt, and full of ‘gumption’!

New Year’s Eve (2011)

This star-studded movie follows an array of characters going through different periods of their lives, all in the lead up to the ball drop on New Year’s Eve. Sparkly and feel good! And with Bon Jovi and Lea Michele starring – you know it has a great soundtrack!

Let It Snow (2019)

Based on the novel by Luke Snellin, this coming-of-age tale follows the lives of several teenagers in a small town learning who they are, and what they want out of life, all on Christmas Eve. Super sweet, and has a killer soundtrack!

How To Be Single (2016)

Four women in New York learn the ins and outs of how complicated dating can be. While this one spans several months, it has a lovely portion spanning the Christmas season. A perfect chick flick for a night in with the girls.

Friends With Kids (2011)

Instead of waiting for the ‘Ones’, two best friends decide to have a baby together to take the pressure off of their biological clocks. Spanning several years, we follow how their family dynamic differs from their friends. Not based solely on Christmas, but has winter and Christmas segments over the years.

Sex and the City (2008)

Four New York women navigate friendship, family, careers, and most of all, love, in this movie based on the T.V. series. Spans several months, including the Christmas and New Year’s season. Full of amazing fall and winter fashion too, if that’s your thing (it’s certainly mine!).

Last Holiday (2006)

Queen Latifah is radiant in this film following a woman who learns she has a terminal illness and only a few weeks left to live – right before Christmas. With nothing left to lose, she embarks on a trip to a beautiful winter resort with only one plan – spend her entire savings account and LIVE. IT. UP. There is an element of romance (in the form of LL Cool J LOL), but this movie is a serious girl power trip!

Just Friends (2005)

Ryan Reynolds singing 80’s romance songs? Anna Faris eating toothpaste with a concussion? Chris Klein being a Nice Guy™? Amy Smart being… well, Amy Smart (who doesn’t love her, seriously – and her name is JAMIE in the movie!)? This movie has it all!

A formerly overweight, high school cheerleader turned svelte, successful record producer, is forced to return to his hometown for the holidays, where he reconnects with his high school best friend (and love of his life).

TO WATCH WITH YOUR MOM…

While You Were Sleeping (1995)

A train station ticket taker is guilted into working on Christmas Day because she has no family (sob). After rescuing a man who was pushed onto the tracks and subsequently knocked unconscious, his family mistakes her for his fianceé. She cannot bring herself to give up her newfound family – even when sparks fly with his brother.

The Family Man (2000)

In this ‘Christmas Story’ reminiscent film, an eternal bachelor and Wall Street executive is given the opportunity to see what his life might have been, had he married the love of his life thirteen years earlier.

Sleepless in Seattle (1993)

After his wife passes away, a man and his young son relocate from Chicago to Seattle. Seeing how lonely his father is, Jonah calls into a local radio station in search of a new wife for his dad. After hearing a heartfelt monologue from Sam himself, hundreds of women write in to the station, including Annie, a newspaper writer from Baltimore. When Jonah reads her letter he is certain she is the one. But can he convince his father?

Christmas with the Kranks (2004)

With their daughter off on a humanitarian trip, empty-nesters Luther and Nora decide to skip Christmas and go on a tropical vacation, much to the dismay of their friends and neighbours. That is, until Blair calls with news that she is returning for Christmas – with her new fiancé.

The Family Stone (2005)

The eldest son of a tight-knit family brings his new girlfriend home for the holidays. The matriarch of the family (Queen Diane Keaton) does not approve of their relationship, and the rest of the family follows suit. After getting off to a rocky start for Meredith, her sister Julie leaves their family’s Christmas to come to her aid – and that’s where things really get complicated.

Love, Actually (2003)

The lead up to Christmas follows 8 London couples through the holiday season, while they learn about love, heartbreak and hardship. The penultimate Christmas rom-com.

Serendipity (2001)

Two strangers meet one New York day while Christmas shopping. They spend a magical evening together, and while Jonathan wants to pursue a romance with Sara, she isn’t so sure. They decide to leave it up to fate, and if their paths cross again, they will know for sure. Years later, both engaged to other people, they can’t stop thinking about one another. Both embark upon journeys to reunite before it’s too late.

I Don’t Know How She Does It (2011)

Sarah Jessica Parker shines in this romantic comedy, following a mother doing what mothers do best – everything. When Kate receives a career opportunity, she struggles to strike a balance between work and family, in the run up to Christmas.

The Oranges (2011)

Two families living on the same street have always done everything together, and are as close-knit as blood.

After moving away to find herself (leaving best friend Vanessa in the dust), Nina begrudgingly returns home for Christmas. Late one night after a family gathering, Vanessa’s father David, and Nina share a somewhat accidental kiss – and decide to pursue their newfound feelings. Utter chaos ensues.

TO WATCH WITH YOUR SISTER…

A Christmas Prince (2017)

An undercover magazine journalist travels to Aldovia, to write a piece on the royal family there. Aldovia has just lost their King, and is preparing for the next in line, Prince Richard to take the throne. To learn more about the royals, Amber pretends to be young Princess Emily’s American tutor, and subsequently is taken in to live in the palace. Once there, Amber quickly grows to care for the family… especially the future King.

A Christmas Prince: Royal Wedding (2018)

Amber and King Richard prepare to wed, but their wedding quickly spirals out of their hands – much to Amber’s sentimental dismay.

The Knight Before Christmas (2019)

A medieval Knight is transported from the 14th century to 2019 in Ohio, after a run-in with a sorceress in the woods near his home. There he meets (and is almost run over by) a young science teacher who has denounced love after a messy breakup. Together they spread Christmas cheer in the small town of Bracebridge, and begin falling in love – until Sir Cole is forced to return home.

Christmas Inheritance (2017)

A young, party-girl heiress is sent to the hometown she doesn’t remember by her father, to deliver a letter to his former business partner – and perhaps learn a lesson in growing up. Fraught with clichés that you can’t hate, this is the PERFECT movie to play while wrapping presents. Speaking from experience here! Plus, Jake Lacy and Andie MacDowell are always a treat.

The Holiday Calendar (2018)

A struggling photographer receives an antique advent calendar from her grandfather for Christmas. At first she doesn’t think much of it, but after the calendar begins displaying some magical forces, she becomes entranced with it.

Holiday in Handcuffs (2007)

Fans of Sabrina, the Teenage Witch, and Saved by the Bell will love seeing Melissa Joan Hart take Mario Lopez hostage in this TV movie. After suffering something of a mental breakdown when her boyfriend dumps her before Christmas, struggling artist Trudie cannot face going home alone (yet again) for the holidays to her judgemental mother. So she kidnaps David, a customer in the diner where she works, and forces him to pretend to be her fiancé for the holidays.

Sunday’s at Tiffany’s

A young woman soon to be married, is visited by her beloved childhood friend, who is all grown up now – except back then he was imaginary, and now he’s real! Based on the book by James Patterson, this is one of my favourite Christmas movies of all time – Alyssa Milano is just wonderful in it.

Northern Lights (2009)

Based on the book by Nora Roberts, a Baltimore homicide detective relocates to a small town in Alaska, to take the position of chief of police and live a quiet life. There he meets Meg, a beautiful but tough pilot with a complicated history.

TO WATCH WITH YOUR KIDS…

Elf (2003)

On Christmas Eve in an orphanage in New York, a baby boy crawls into Santa’s sack and is transported to the North Pole. Once there, he is adopted by Papa Elf and raised as one of Santa’s elves. Buddy quickly outgrows his elfin lifestyle, and Santa breaks the news to him that he was not born there. Santa confides that Buddy’s biological father is on the naughty list, and sends him to New York to help his father become a better person. While there, Buddy falls into a job in a department store in the store’s Santa Land, and subsequently falls in love with a beautiful employee there.

Beauty and the Beast (2017)

The classic tale of Beauty and the Beast, brought to life with plenty of magic, love, and friendship. Of course lots of snow, and winter scenery as well.

Harry Potter and the Deathly Hallows Pt. 1 (2010)

All of the Harry Potter movies have wonderful winter and Christmas scenes, but the last two movies are where all of the characters come-of-age and start looking at each other a little more… romantically.

In this movie, Harry, Ron and Hermione embark upon a journey to find, and destroy, the remaining Horcruxes. Along the way their relationship dynamics becoming blurry.

Harry Potter and the Deathly Hallows Pt. 2 (2011)

And in this one, true feelings come to light between several of the characters. It is also the final chapter of the series, and follows the trio, and ultimately all of the characters, through to the final battle with Voldemort.

The Princess Switch (2018)

A small town baker and a duchess (and fianceé to a future King), long for a change of scenery. After a chance meeting where they realize they look so similar they could be identical twins, they decide to trade places to see if the grass really is greener on the other side.

Holiday In The Wild (2019)

A newly empty-nester and former veterinarian is immediately dumped by her husband, right after their son leaves for college. Devastated and lost, she decides to go solo on the trip to Zambia she had booked to surprise him for their second honeymoon. After a rocky start with her pilot, she helps him in aiding in the rescue of an abandoned baby elephant, and quickly falls in love with Africa.

*This movie takes a little bit of an educational approach, and your kids will love all of the wildlife shots, and learning about elephants! I was not unpleasantly surprised by this, I actually really enjoyed the educational aspect.

Frozen (2013)

I almost filed this one under ‘Watch With Your Sister’, but as it is a children’s movie, I’ll leave it here!

Two princess sisters grow up closely, until a tragic accident leaves one sister with no memory of the other ones magical powers. After they lose their parents at sea, the princesses drift apart. When eldest sister Elsa comes of age and takes the throne, her coronation day goes terribly wrong. After freezing the town of Arendelle into an eternal winter, she flees to the mountains. Younger sister Anna sets out to find her with the help of an iceman, his reindeer, and a talking snowman.

While this movie is most definitely about sisterhood, love and friendship, Anna does find romantic love in an unlikely place!

*Frozen 2 is now in theatres!

Snow Day (2000)

A small town is completely shut down due to a massive snow fall. Several stories intertwine over the course of one day, with one of them following high schooler Hal as he tries to win the affections of the most popular girl in school, Claire.

Snow Globe (2007)

A young woman sick and tired of her family’s chaos, dreams of a perfect Christmas with no drama. She receives a snow globe in the mail one day, and when she goes to sleep that night, she wakes up in the small village inside. Everything is perfect inside the snow globes world, and she begins spending more and more of her time asleep, and less time in real life.

Jack Frost (1998)

This classic story of Frosty the Snowman meets Jack Frost, follows a young boy who’s father dies in a tragic car accident while making his way to his family for Christmas. A year later, after playing a tune on his musician dad’s harmonica, Charlie brings Jack’s spirit back, where it takes residence inside the snowman Charlie built.

While this movie is mostly lighthearted and fun, it is also deeply heartfelt, especially when it comes to Jack and Gabby’s marriage. You might have to hide a tear or two!

The Nightmare Before Christmas (1993)

A dark fairy tale, this movie follows the Pumpkin King of Halloween Town, Jack Skellington, who has grown weary of Halloween, and longs for change. He wanders into the forest one day and comes across a series of doors in the trees. He takes the one to Christmas Town, and loves it so much he wants to take it over himself. Meanwhile, a beautiful rag doll is secretly in love with Jack.

*Darkly complicated, save this one for older children, as it may be a bit scary for a younger audience! If in doubt, this is a good one to watch with a spouse instead.

Ice Age: The Meltdown (2006)

A trio of Ice Age animals journey across the valley they live in, to board a boat on the other side. It has been predicted that a flood is coming, as the ice wall they live below is melting, and it is holding back a massive lake. Along the way, Manny meets Ellie, another mammoth, after it was thought that he was the last remaining mammoth on earth.

TO WATCH WITH YOUR SPOUSE…

Two Night Stand (2014)

After an awkward one night stand, a snowstorm forces two people to spend another night together, and they might just have to get to know each other in the process.

Four Christmases (2008)

A couple that always vacations for Christmas finds their plans to escape thwarted on Christmas Day. Thus begins the longest Christmas Day of their lives, as they must visit all of their estranged parents, one family at a time. Along the way, they learn that their life together may not be as perfect as they once thought.

Winter’s Tale (2014)

A supernatural love story following a young man marked for death, who meets a beautiful, but terminally ill young woman while trying to rob her family’s home.

The Huntsman: Winter’s War (2016)

A fantasy adventure film taking place both before, and after Snow White and the Huntsman. The main storyline follows Eric and Sara, a young couple trying to decipher their relationship after being reunited, 7 years after being tricked apart by a sorceress.

Deadfall (2012)

A crime drama following two siblings on the run after a casino heist gone wrong. They split up after their getaway driver is killed, with Addison continuing the crime spree solo, and Liza running into a recently released prison inmate with whom she falls in love.

Die Hard (1988)

New York cop John McClane travels to LA to visit his wife Holly, for Christmas. He arrives at the high-rise where she works in time for her staff Christmas party, and things are off to a rocky start when he sees that she is going by her maiden name in LA. While John is in the bathroom changing, German terrorists take over the party and kill Holly’s boss. With John being the only one to slip away and escape, he must now work to save the group, and his wife, before things get worse.

Sugar Mountain (2016)

Two brothers are running their mother’s tour boat business into the ground. After receiving a notice of closure that gives them only month to come up with the money to save their boat, they come up with a plan to fake a survival story to make a quick buck with the press. However elder brother Miles, who is inexperienced in the wilderness, never makes it to the hideout they agreed upon, and really does go missing. And to the world, it looks like younger brother Liam did it – to get to Miles’ girlfriend, Lauren.

The Snow Walker (2003)

*BONUS* This amazing movie is Canadian!

Set in the 1950’s, a Canadian former WW2 bomber pilot is coerced into taking aboard a sick young Inuit woman, while on a routine supply run. While on their way back, the plane malfunctions and they crash land in the middle of the Northwest Territories. Their roles are reversed when she, while succumbing to her illness, teaches him how to stay alive in the middle of the tundra.

Based on the short story Walk Well, My Brother by Farley Mowat.

The Day After Tomorrow (2004)

Follows, three separate, but interwoven storylines. After a climate shift in Antartica triggers a new Ice Age across the Earth, a paleoclimatologist father treks across a frozen wasteland from Washington D.C. to New York, to reach his teenage son who is on a school trip. Sam is now trapped in the New York public library, with several other survivors, including classmate Laura, whom he is secretly in love with.

TO WATCH BY YOURSELF…

Watch these alone so you can ugly cry!

Five Feet Apart (2019)

Two teenagers both living with cystic fibrosis, meet when Will comes to stay in the hospital Stella lives. Stella tries to ignore Will at first, but he quickly wins her over and the two begin a romance. The only catch is that they cannot touch each other, ever.

The Mountain Between Us (2017)

Strangers meet at an airport when their flight to Denver is cancelled, due to bad weather. With each having an important reason to get to Denver ASAP, they agree to hire a private plane together. Halfway through the flight, their pilot suffers a fatal stroke. The plane crash lands into the High Uintas Wilderness, leaving them with only each other to survive.

Titanic (1997)

Follows 17 year old Rose, who is engaged to be married to a power hungry man she does not love. Rose is a first-class passenger aboard the RMS Titanic with her fiancé, Cal, and her mother Ruth, traveling to New York. Ruth has pressured Rose into the engagement, and one night a distraught Rose considers suicide to escape her fate. Jack, a poor artist and third-class passenger, stops Rose from jumping from the stern of the ship, convincing her that it is not worth it. As Rose tries to come back over the railing, she slips, and Jack saves her. The two quickly fall in love, in this bittersweet romance.

Eternal Sunshine Of The Spotless Mind (2004)

In this futuristic drama, Joel and Clementine meet on a train from Montauk to Rockville Centre, both for seemingly no reason. We learn that they used to be in a relationship, and each had had a procedure done where they had their memories of each other erased by a technician. They are immediately drawn to each other, and feel an intimate connection even though they are glaringly opposite. The movie follows Joel’s erasure of Clementine, and revisits his memories of her.

In Your Eyes (2014)

For fans of Joss Whedon’s Firefly, comes this paranormal love story about a man and a woman, that for whatever reason, can hear each other’s thoughts, and see each other’s worlds, from across the country. Rebecca lives in New Hampshire with her husband Phillip, a doctor, and Dylan lives in New Mexico – alone in a trailer, having just been released from prison. Once the two realize they are connected, they become fast friends, sharing in their day to day lives, until they both realize they feel something more.

Untamed Heart (1993)

Christian Slater and Marisa Tomei are magic in this film, revolving around two working class people. She’s a young woman in beauty school, moonlighting as a waitress in a diner part-time, where he’s a busboy that keeps to himself. One night while walking home after her shift at the diner, Caroline is attacked by two men. Adam appears out of nowhere and fights them off, sparking a romance between the two as Caroline sees Adam in a whole new light.

AND HERE ARE THREE NEW ONES COMING SOON THIS CHRISTMAS SEASON:

Frozen 2 (2019)

The gang travels to an enchanted land to learn the origins of Elsa’s powers.

Last Christmas (2019)

A woman working a dead end job in a year round Christmas shop meets a man that turns her world upside down.

A Christmas Prince: The Royal Baby (2019)

Amber and Richard prepare for the birth of their first child.

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I hope you enjoyed this list!!! And I hope there was plenty on it that you hadn’t heard of, or had forgotten about. If you liked this post and want to see more like it in the future, please subscribe to my blog to get email updates! Or follow me on Instagram, I’m very active over there.

Have the Merriest of Christmas seasons friends, and let me know if I missed any of your favourites. I’ll be adding to this list as new movies come out!

xo,

Jamie

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