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14 Best Valentine’s Day Movies

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To borrow a slogan from, Sex and the City, “And just like that,” Valentine’s Day is upon us once again. It is a great time to curl up at home, with a partner, with family, friends, and yes, even alone. Whoever you’ve decided to spend Valentine’s Day with, we have selected 14 best Valentine’s Day movies for you to watch this year.

For most of us, Valentine’s Day brings up a lot of emotion. While there are enough of us who shrug it off as just another day, it’s hard to ignore the attention that the day demands, given the marketing genius of those selling anything from chocolates to romantic getaways. While there is nothing wrong with chocolates or getaways of any kind, sometimes, it’s just not that kind of Valentine’s Day.

pink marshmellows valentines day movie suggestions

Sometimes, watching a rom com on Valentine’s Day is a nice way to mark the day, while bringing in joy, and setting some time aside for your well-being. It’s low key enough that you can do it after a nice dinner, romantic or not.

And why not?

This year, Valentine’s Day falls on a Wednesday, so for those of us who have a busy workday in the morning, we may not feel like going out and painting the town red.

The great thing about each of these movies is that they are fun. It’s also the one time that lends itself to allowing some chocolate snacking without feeling like you are going down an unhealthy road. If you can’t have some nice chocolate on Valentine’s Day, then when can you? Good chocolate goes especially well with watching our best Valentine’s Day movies, doesn’t it?

For the chocolate part, you know your favourite, so hopefully, you can indulge a little.

As for the best Valentine’s Day movies, below is what we used to determine our suggestions for you:

popcorn to watch 14 best valentine's day movies

Laughter

For those who love to laugh at love, and laugh we should. People do silly things when in love, and in search of love. It’s good when we can laugh at ourselves, and in each of these films, we can laugh with these characters.

The journey

Love is a positive emotion, and we get to enjoy the character’s journeys to finding love. In a film, we can usually spot the person the protagonist should be with, and the one they should run away from, and fast! Still, even in a romantic comedy, there may still be some hiccups along the way, before the happily ever after, anyway.

Love should be a good thing

These films also reaffirm the belief in the power of love. They remind us of the benefits of having a great love in our lives.

Ah, the scenery, the story…

Many times, romantic comedies take place in unique settings and they take us away so we can enjoy a bit of an escape from the ordinary in our day. Besides, even if a story is set in a more familiar location, the romance and the comedy can take us into another story, so that we can return to ours, to our own love story.

14 Best Valentine’s Day Movies for you:

Most of these have been around for awhile. Fairy tales never get old, really, and neither do good romantic comedies. In no order of preference, here goes…

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My Big Fat Greek Wedding

This is an oldie, but so very funny, that it deserves another viewing. We love a good reinvention story, and the protagonist, Toula (played by Mia Vardalos), is considered an old maid by her family and she’s only about 30! Times have changed since this movie came out, and it wasn’t even that long ago. The protagonist undergoes a transformation as she falls in love, and the road to a happily every after is endearing. What’s really fun about this film is the clash of cultures between Toula’s Greek heritage and her love, played by John Corbett, and how love conquers their differences.

The Princess Bride

We don’t know what it is about this movie, but it captivates even the most cynical of souls. It’s a fairy tale. There is a beautiful princess (played by Robin Wright) and a handsome hero (Cary Elwes), and many other memorable characters, including an evil prince. There’s only one thing about this film that doesn’t work, and that happens early on when the hero fights off a gigantic something (you can’t miss it). Everything else about the film is delightful. There are also some great lines in the film that are over-the-top hilarious.

pink cupcakes

While You Were Sleeping

This one has been around for a while, but it’s a good film. Our hearts go out to Lucy (played by Sandra Bullock, who leads a lonely life, and harbours a secret crush on a very good-looking man (Peter Gallagher), who passes her daily with barely a glance. When he lands in a coma, she goes to see him in the hospital. When people assume she is his significant other, she goes along with the lie that they are engaged. The sheer nerve of the lie is something that seems out of character for Lucy, but she is so lonely and no harm comes to her love-interest that we can forgive her. Plus, it sets up a wonderful complications when she meets the love-interest’s brother (Bill Pullman), and they begin to have feelings. Does she recover from the lie and find true love? Of course! That’s part of the appeal of romantic comedies. Shakespeare himself seems to chime in with, “All’s well that ends well.”

How to Marry A Millionaire

This is a classic, and it still entertains. It stars Marilyn Monroe, Lauren Bacall and Betty Grable as Manhattan roommates looking for rich men to marry. It’s lighthearted and fun and a bit crazy, given that the women go to great lengths to appear more affluent than they are. There’s some interesting social commentary on marriage and dating, which is still relevant today. If you are feeling nostalgic, then this is a fun one to watch.

woman in pink dress

Bride and Prejudice

Jane Austen is always fun, and this is a play on Pride and Prejudice. The film centers on an Indian family with unmarried daughters. Aishwarya Rai plays Lalita, who falls for Will Darcy, played by Martin Henderson. There are several locations and Bollywood elements (the dancing), and this, along with the characters, makes for a pleasant watch. It’s definitely an uplifting film.

Wedding Crashers

This one is interesting because it’s from the viewpoint of the men, two best friends played by Vince Vaughn and Owen Wilson. They don’t start off being nice people. The dual spend their free time crashing weddings, and bedding women they are dishonest with. Then there’s one wedding they attend that sets things in motion, and they begin their own separate journeys to falling in love, and becoming better people. The love interests are Isla Fisher (who delivers a hilarious performance) and Rachel McAdams (who plays her sister).

Think Like a Man

The film (2012) is based on Steve Harvey’s 2009 relationship advice book, Act Like a Lady, Think Like a Man: What Men Really Think About Love, Relationships, Intimacy, and Commitment, which was very well received when it came out. It was unique in that it was one of first popular books lifting the curtain on how men viewed the women they dated by the actions they took. The film is a fun rom-com with Gabrielle Union, Jerry Ferrara and Kevin Hart.

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Bridget Jones’s Diary

Renée Zellweger plays Bridget Jones, who is in her early 30s, single and apparently fat (not at all). The actress had to gain weight for the role, so it was a big deal at the time that she be heavy, which is apparently an obstacle to love. Ridiculous, right? Despite this silly premise, the movie is very funny, and Bridget and her band of friends, along with her family, are heartwarming in their closeness. Over the Christmas holidays, she “meets” (knew him in childhood) the very successful, recently divorced and handsome Mark Darcy (Colin Firth). It’s a clash of class. He is wealthy and she is middle-class. He is a human-rights lawyer and she is in media. He is refined. She is not. However, she sure is fun, and their romantic journey is too. It borrows a lot from Pride and Prejudice, which incidentally, Colin Firth started in as Mr. Darcy.

Crazy Rich Asians

This is a totally feel-good, escape film for Valentine’s Day. We follow New Yorker, Rachel Chu (Constance Wu) as she journeys to Singapore. Her boyfriend, Nick Young (Henry Golding), comes from an extremely wealthy background. The secondary characters are likeable and the setting is opulent and the lives of the ultra-wealthy, very out of the ordinary for most of us, so it’s a good escape. It’s really very fun and funny.

fuzzy slippers next to laptop

It Happened One Night

This one is from 1934! It was huge at the Oscars the following year. With Oscar season coming, why not? It won in five categories. Romantic comedies don’t usually fare well at the Oscars, which is a shame. It would be great to have a comedy category, wouldn’t it? It stars Clark Gable as a reporter and Claudette Colbert as a runaway heiress, as they are forced to team up when their bus leaves them behind. Remember the classic scene where a man tries hitchhiking to no avail, but then the lady shows some leg as she is hitchhiking and a car stops? That’s this film.

Last Holiday

There is something about films where women transform themselves and their lives that appeal to us both. Yes, with art (and let’s not be snobby about rom-coms as there is room for all genres in art, even if they don’t exactly win Pulitzers or Nobel Literature prizes) there is supposed to be a transformation, a character arc. This is the magic of literature, but you still can enjoy the transformation in a good rom-com. The film starts off with a hard-working and frugal Georgia (played by Queen Latifah) living a dull life working in a department store with two secret loves: cooking and her good-looking co-work, Sean (played by LL Cool J). When her doctor tells her that her CT scan showed that she only weeks left to live, she takes off on a last holiday. She heads off to a winter wonderland: the Grandhotel Pupp in the Czech Republic, where a famous chef appreciates her tastes, and befriends her. She also meets some influential people who assume she is also influential, although she is transparent about her position. While she is enjoying her life, her crush sets out to find her. And that CT scan? It’s a feel good resolution.

Shakespeare in Love

So, Shakespeare knows something about love, having written many romantic comedies, and Romeo and Juliet. In this film, Shakespeare (played by Joseph Fiennes) is the protagonist as a young writer in London, during the Elizabethan period. When he meets Viola (played by Gwyneth Paltrow), his writing comes to life, as does a blooming romance that is forbidden because of class (and also due to the fact that he has a wife back in the countryside who we are led to believe that he is separated from since we are led to feel no sympathy for Anne Hathaway — the wife, not the actress, of course). Dame Judy Dench, Colin Firth and Ben Affleck are also part of the cast. It’s a delightful film, and if you enjoy Shakespeare or theatre, you’ll probably enjoy the film.

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Under the Tuscan Sun

Diane Lane plays Frances, who buys a house to restore in Tuscany while on a get away to heal from the heartbreak of a cheating husband who ends up with her mother’s house. One of the reasons being that it’s in a good school district. He didn’t want children with her, but it appears he does want children with someone else. Ouch. This film charts the meandering road of love, and serves as a reminder that on this road, we continue to live our lives and sometimes, who we think is the one, is so not. Rest assured, there is a happy ending, although the movie itself is about a woman reinventing her world once her marriage ends. The scenery is spectacular, as you can imagine.

Past Lives

This is the most recent on our list, and it going into the 2024 Oscars with two nominations. In the film, Nora (played by Greta Lee) says, “There is a word in Korean – inyeon. It means providence or fate.” It’s a beautiful film raising all sorts of questions about fate, about choice, about love.

We’d love to hear from you! Do you have another film suggestion?

-Isabel and Marilyn

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We share of love of Lisbon, Chihuahuas, sushi, coffee, binge-worthy tv, movies, being out in nature, the ocean, and our amazing mom.

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We're Isabel and Marilyn, the two sisters behind Letters and Lipstick.









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