The Best Movies to Watch on Valentine’s Day, Whether You’re Coupled Up or Solo
Courtesy of Netflix/A24/MGM/Sony/Disney
Valentine’s Day is a divisive holiday, even for people in couples. Some like to celebrate, some don’t, some take it seriously, and some just take advantage of all the available chocolate at the drugstore. If you happen to be craving a little romance regardless of your relationship status, there’s definitely a movie out there with exactly the type of loving feeling you’re looking for. Below is a list of romantic comedies, dramas, period pieces, and even films about Valentine’s Day itself to watch when you come home from dancing with your honey—or if you’re hibernating all night solo.
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The title says it all. Valentine’s Day is comprised of multiple intertwined love stories, starring some of the most popular actors of the mid-aughts including Jessica Alba, Jessica Biel, and Ashton Kutcher. As the big day unfolds in Los Angeles, some of them win in love while some of them lose, though they all connect with one another in the end.
Kennedy’s (Hilary Swank) beloved husband Gerry (Gerard Butler) passes away young, leaving her to pick up the pieces of her life without him. She discovers he’s left her one last gift, a series of letters he wrote for her to receive over the next year, starting on her 30th birthday. A movie about loss, grief, and the eternal power of love, this film really takes viewers through every emotion. And it even manages to have a happy ending.
Sasha (Ali Wong) and Marcus (Randall Park) grew up together in San Francisco, where Marcus’ family embraced her as one their own. But after a major loss for both of them, their friendship is suddenly severed. Fifteen years later, their paths cross again and they get a second chance at being the love of one another’s life. Funny and oozing with with lead character chemistry, this movie also features a very memorable appearance from Keanu Reeves.
Fans of director Nia Vardalos will never get sick of watching her fall in love with John Corbett. (Though this is a completely different story, it’s basically a part of the My Big Fat Greek Wedding extended universe.) Genevieve is a florist and Greg a restaurateur. Their jobs certainly bring them in touch with romance, but they struggle with love in their interpersonal lives. When they decide to date according to Genevieve’s five-date rule, they might not be ready to part at the end.
Cher plays a woman who long ago gave up on anything close to passion. She’s planning an engagement to her longtime boyfriend who is a bit of a mama’s boy. While he’s away to see mom, she decides to reach out to his brother to forge a reconciliation. That brother is played by the delightfully deranged Nicolas Cage, a one-handed baker who has Cher letting her hair down under the full moon again.
Simon has been emailing another teen boy, and he’s slowly falling for him. The only problem is, he doesn’t know who is on the other side of the screen. This coming-of-age story is about how complicated falling in love can be when it’s so tied up with your entire identity. It’s the kind of teen romance LGBTQ+ viewers deserve to see much more often—happy ending included.
One movie of a longstanding series about friends finding love, this entry follows writer and single man Harper Stewart, played by the gorgeous Taye Diggs. It turns out Harper’s next book is based on the life of his close friends, which he doesn’t want them to know about pre-publication. The author is all set to be the best man at his bestie’s wedding when an early copy threatens to blow up his plan.
What’s Valentine’s Day without some romantic music? (And some big dance numbers too?) Ryan Gosling and Emma Stone have as much chemistry as ever, playing a taciturn jazz musician and an up-and-coming actress—two people who help each other discover the best of themselves in the industry world of Los Angeles.
To All the Boys I’ve Loved Before
Every time Lara Jean Covey (Lana Condor) has fallen in love in her life, she’s written the object of her affectionate a deeply heartfelt letter…and then she puts it in a box, never to be discussed. But when her letters somehow get let loose, so do all the feelings Lara Jean has been trying to keep inside. She finds out what it means to really connect with someone she loves.
For people celebrating Valentine’s Day ironically or for couples who connected over their love of horror, My Bloody Valentine is a twist on the old Bloody Mary urban legend. A bunch of young friends get together to celebrate the holiday, conjuring a legendary murderer to the scene. Chaos ensues.
American tourist Jesse (Ethan Hawke) is on his way to Vienna when he meets Parisian student Celine (Julie Delpy), who is on her way home. A casual conversation on the train suddenly gets deep, and he convinces her to spend his last night in Europe with him in Vienna, since he doesn’t have the money for a hotel. In one night, they discover how even brief love can be life changing.
For a little modern history with your romance, the film Southside With You is based on the first date President Barack Obama and First Lady Michelle Obama shared in Chicago, back in 1989. At the time, he was a starting out as a law associate and Michelle was an attorney—they didn’t know what was to come. This historical love story is all about being present in the moment with the person you love.
Queen Latifah plays a quiet woman named Georgia who has always been one to fade into the background. When she is diagnosed with a terminal illness, she decides to live the life she’s always been afraid to before it’s too late. While this movie does have a romance, it’s also about the importance of loving yourself enough to go for what you want.
Julianne (Julia Roberts) and Michael (Dermot Mulroney) are best friends who made a pact to get married if they are both single at the ripe old age of 28 (!), which she never took all that seriously. Until Michael gets engaged to someone else. Julianne quickly realizes what she’s losing and spends most of the movie acting exactly how love makes us feel sometimes: crazy. But in the end, she discovers that really loving someone means doing what’s best for them.
Set in the mid-’80s, this movie stars rom-com favorites Adam Sandler and Drew Barrymore. Sandler is a wedding singer who gets dumped at the altar, which takes a toll on his career. But then he meets Barrymore’s Julia and they hit it off—the only problem is she’s already engaged.
Natasha Lyonne plays a cheerleader who doesn’t realize that her lack of interest in her jock boyfriend isn’t typical of her friend group. Her parents send her to conversion therapy at True Directions, a boot camp for making teens straight. That’s where she meets Clea DuVall’s Graham, who helps he come to terms with her true self through the power of love.
10 Things I Hate About You
This modern re-telling of Shakespeare’s The Taming of the Shrew is about two sisters, one sweet and one sour. The former is angelic Bianca, who isn’t allowed to see boys until her older sister Kat starts dating. Only problem is, Kat’s (Julia Stiles) abrasiveness is keeping all the boys away. So, the new kid who wants to take Bianca to a formal dance ends up paying the scariest boy in school (Heath Ledger) to woo Kat, but things soon get complicated for everyone involved as real feelings form.
Barry Jenkins’ heartbreaking Best Picture winner follows Chiron through three periods of his life, as a boy in Miami, during the traumatic events of his teenage years, and in his isolated adulthood. From a young age, the people around him know he is gay, with some reacting with violence and derision, others with tenderness and care. This isn’t exactly a story with a happy ending, but it is about the way love forms and guides people their whole lives.
Lloyd (John Cusack) is a goofy teen with a thoughtful, eclectic mind who isn’t necessarily headed anywhere until he meets Diane (Ione Skye), his archetypical opposite. The straight-A student is heading for big things, but after graduating, she realizes how much she missed out on during her school years. Their relationship allows them both to see parts of the world they never would otherwise.
Can a man and a woman ever really be friends? It might not be the most modern question, but the charming performances of Billy Crystal and Meg Ryan keep it interesting decades after its release. Their well-drawn, funny relationship as friends earns the audience’s hope they’ll fall in love, and this movie delivers with one of the best Big Moment speeches ever dedicated to film.
Rachel Chu (Constance Wu) has been dating boyfriend Nick (Henry Golding) for a while when he invites her to Singapore to meet his family and attend his BFF’s wedding. Only when they’re on the most luxurious plane ride ever does she realize Nick isn’t exactly who she thought he was. He and his family are basically local celebrities and the richest people in town. To keep Nick in her life, Rachel needs to make some tough choices as she comes up against his mother (Michelle Yeoh) and her extreme disapproval.
Portrait of a Lady on Fire
If you want a romantic movie full of longing looks and a side story about family planning, this is the historical drama for you. A young woman is going to be married far from home as soon as her promised fiancé receives a flattering portrait. So she keeps smashing paintings to stall their union. Then, a female painter arrives and her mother leaves town for the weekend. Sparks fly.
Bridget Jones was one of the most well-known single ladies of both book and film, but her inability to get her life together is the biggest part of her charm. Based loosely on Pride and Prejudice, Bridget falls in love with the wrong man while the haughty right man is just under her nose. Luckily, she works it out in the end.
Eternal Sunshine of the Spotless Mind
In this film, anyone can have their memory of a person removed—a popular procedure for the heartbroken. A man receives a notice saying that his ex has erased him and decides to follow suit as an act of revenge. As he goes through the process, he comes to understand exactly how much he’s losing by forgetting both the good and the bad.
Again based on Austen’s Pride and Prejudice, this modern adaptation focuses on four beautiful daughters who have a nosy mother desperate to find them husbands. Their oldest daughter, Lalita (Aishwarya Rai), only wants to marry for love. She meets William Darcy, and American man unlike anyone else she knows. Can they make it work? On Valentine’s Day, absolutely.
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