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Valentine’s Day has a reputation for being quite controversial. If you’re in a relationship, then there’s the pressure of making sure you get the day right. Good reservations. Great gift. Steamy end to the night. Lather, rinse, repeat the same anxiety every year. And if you’re single, it’s a reminder that seemingly everyone else in the world is in a relationship except for you. Y’all: neither of those things are actually true. Perfect doesn’t exist. Not everyone is taken. Valentine’s Day is, frankly, a bunch of bullshit.
But fear not: it is the perfect day to dive into the canon of great Valentine’s Day movies, which are available and enjoyable for all. Maybe this year, instead of trying to do something grandiose (or wallowing in the loneliness), consult this list and get the night in you deserve. There are classics in here along with new favorites. Saccharine sweet looks into the Hallmark holiday and slightly more jaded fare. The short of it is this: there’s something for everyone this Valentine’s Day. Relationship status be damned.
Be the chocolate stained, wine-addled Valentine you wish to see in the world.
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She’s Gotta Have It
This is one of Spike Lee’s greatest (and the one that put him on the map). The 1986 film follows one woman who manages to date three different men at the same time, refusing to settle for just one. A woman’s got to live her life, you know? This is a perfect Valentine’s Day film because it scratches the itch of the romantics out there, but let’s say this: it also gives a big nod to those who prefer to live an untethered life.
Palm Springs
This one is for the people in the back who are over love. Sometimes, the best love stories are the one that come from the cynical perspective. Andy Samberg stars in this time loop movie (we love time loop movies!) about a guy who can’t escape one fateful wedding day, stuck in an existence of isolation… until someone else gets stuck in the loop with him.
Sleepless in Seattle
After Sam Baldwin’s wife, Maggie, dies, he and his son, Jonah, move from Chicago to Seattle for a change of pace. But once Jonah sees that Sam (Tom Hanks) is still lonely, he takes his father’s love life into his own 8-year-old hands. On Christmas Eve, he calls Dr. Marcia, a popular radio host, and tells her that his dad needs to find a woman. Soon, the letters start pouring in from all over the country, and Annie Reed, an engaged reporter in Baltimore, sends one of them. She proposes they meet at the top of the Empire State Building on Valentine’s Day, just like in the movie An Affair to Remember (1957). This movie also features Tom Hanks’s real-life wife, Rita Wilson.
Someone Great
Someone Great flew under the radar when it came out last year, but the almost anti-romantic comedy starring Gina Rodriguez ends up being as much about friendship as it does about love.
Love Simon
Hey! Look at that. We can put two gay romances on a line up without anyone having to die a tragic death. That’s called growth in cinema. A rom com in its own field, Love, Simon tells the story of Simon, a high schooler who struggles to come out of the closet after falling for an online suitor who is struggling with his own sexuality.
Hitch
The Bridges of Madison County
This 1995 movie starring Meryl Streep and Clint Eastwood will get the even the toughest nut crying by the end. The film, about Francesca Johnson, a 1960s Italian-immigrant housewife in Iowa who meets and falls in love with a drifter photographer for National Geographic, is adapted from the 1992 book of the same name. The film was also directed by Clint Eastwood, who cast himself in the lead role of the dashing mysterious Robert Kincaid from Washington state. Streep does an Italian accent with a slight Iowan lilt that will make you just want to quit trying anything, because she’s already mastered it.
My Best Friend’s Wedding
Julianne Potter (Julia Roberts) and her best friend, Michael O’Neal (Dermot Mulroney), had a deal that if they were both single by the time they were 28, they would marry each other. Four days before Julianne turns 28, she finds out that Michael is engaged to be married to a 20-year-old woman named Kimberly (Cameron Diaz). Julianne realizes that she doesn’t want Michael to marry anyone but her, so she plots a way to break up the wedding. This movie includes a very enthusiastic rendition of “I Say a Little Prayer” that is just begging to be emulated at actual weddings or rehearsal dinners as much as possible.
The Big Sick
In 2017, comedian Kumail Nanjiani and his wife, writer Emily V. Gordon, brought their real-life story to the screen, via this romantic comedy based on how they really fell in love. The movie stars Nanjiani as himself, and Zoe Kazan plays Emily, who in the film and in real life, fell mysteriously very ill right after she and Kumail called it quits. Emily’s parents, played by Ray Romano and Holly Hunter, fly in to care for their daughter while she is in a coma in the hospital. Meanwhile, Kumail tries to prove that he is the person for Emily, with whom he’s still very much in love.
Notting Hill
Julia Roberts is a bit of a romance movie master. In this other beloved 1990s rom-com, Roberts plays a famous actress, Anna Scott, who just wants a normal life. In London’s charming neighborhood, Notting Hill, she meets awkward British bookshop owner, Will Thacker (Hugh Grant). Will and Anna fall in love, but their lives prove very different, which is a major roadblock for their quirky relationship.
10 Things I Hate About You
Based on William Shakespeare’s The Taming of the Shrew and set in Seattle in the late 1990s, this movie takes 16th-century comedy to the Pacific Northwest grunge scene. Kat Stratford (Julia Stiles) is a highly intellectual teen who doesn’t have any interest in the irresponsible lifestyles of normal teenagers. She’s nicknamed “the shrew,” but her younger sister, Bianca (Larisa Oleynik), wants to date, go out, and be a normal high schooler. The only problem? Their father won’t let Bianca date unless Kat does. Cameron (Joseph Gordon-Levitt), a new student at the school, pays school bad boy Patrick Verona (Heath Ledger) to take out Kat so he can have a shot with Bianca. Nothing could go wrong with a deal like that, right?
Crazy, Stupid Love
At the beginning of this movie, Emily Weaver (Julianne Moore) tells her former high school sweetheart and husband, Cal Weaver (Steve Carrell), that she wants a divorce. Then, Cal pulls a full Ladybird and jumps out of the car, signaling how he feels about the whole thing. Enter Jacob (Ryan Gosling), who finds Cal wallowing at a bar and teaches him how to be a suave man of the 21st century. And y’all: that’s only about the first 15 minutes of the film.
The Last Five Years
Are you in the best years of your relationship to date? Wow, this film is for you. Are you in the worst years of your relationship, or dare I ask, completely out of it? Wow, this film is for you. All that you really need for this film is a love for Anna Kendrick and Jeremy Jordan’s singing voices, as well as a light understanding of the concept of “love.” The rest is the journey of two people who tell the musical story of their relationship. One begins at the beginning and moves forward. One begins at the end and moves back.
While You Were Sleeping
This is technically a Christmas movie, but it does just fine at Valentine’s Day, too. It’s set in the cold Chicago winter, when transit worker Lucy Moderatz (Sandra Bullock) pulls her crush, Peter (Peter Gallagher) off the train tracks after he falls and hits his head. Peter ends up in a coma, and his whole family is under the impression that he and Lucy are engaged. Knowing that Peter doesn’t even know her name, Lucy decides to go along with it, and while he’s asleep in the hospital, she spends the holidays with Peter’s family. While Peter is sleeping, she also falls in love with Peter’s brother, Jack (Bill Pullman). This sounds like a lot to happen in one movie, but just trust that it’s a good one.
Moonstruck
This plot is not unlike While You Were Sleeping in that it’s about a woman who falls in love with the brother of the man she’s supposed to be with. Widow Loretta (Cher) accepts a marriage proposal from her boyfriend, Johnny (Danny Aiello), but she falls for his younger brother, Ronny (Nicolas Cage). But this isn’t the only secret romance going on in this family. Cher won an Oscar for this one in 1988, and that was also the year of that famous Bob Mackie dress.
When Harry Met Sally…
You’ve Got Mail
Nora Ephron’s remake of The Shop Around the Corner for the digital age stars Meg Ryan as a Manhattan bookseller whose business falters when a big-box bookstore run by a devious Tom Hanks moves into the neighborhood. But little do these enemies know, they have fallen in love with each other while communicating anonymously via email.
Love & Basketball
The Notebook
Casablanca
The classic drama is one of the greatest romantic movies ever made. Humphrey Bogart and Ingrid Bergman star as two former lovers who unexpectedly reunite in Morocco during WWII, and their reunion is disrupted when the woman needs her old flame’s help to escape—along with her new husband—to America.
Eternal Sunshine of the Spotless Mind
Crazy Rich Asians
Blue Is the Warmest Color
Titanic
James Cameron’s Oscar-winning masterpiece is one of the great technical feats in the modern Hollywood era, but it also features the compelling love story between a poor artist (Leonardo DiCaprio) and a upper-class debutante (Kate Winslet) who have an affair aboard the infamously doomed RMS Titanic.
Love Story
Erich Segal’s bestselling novel became a Hollywood classic, with Ryan O’Neal playing a young Harvard man who meets—and falls in love with—a working-class Radcliffe student played by Ali MacGraw. Their relationship is tested, in classic weepy fashion, when she’s stricken with a terminal illness.
Brokeback Mountain
To All the Boys I’ve Loved Before
Lara Jean (Lana Condor) is your typical lovelorn teenage girl who drafts love letters to her former crushes for her eyes only. But when the letters wind up being mailed to the former objects of her affection, her life is turned upside-down—and she finds unexpected romance in this comedy based on Jenny Han’s novel.
The Princess Bride
Romeo + Juliet
The seminal love story about a pair of doomed, star-crossed lovers got the Gen-X treatment with Baz Luhrmann’s brash and inventive reimagining of William Shakespeare’s most famous play. Leonardo DiCaprio and Claire Danes star as the teenage lovebirds, whose feuding families keep them apart—and whose love story meets a tragically romantic end.
Ghost
This 1990 tearjerker proves that death isn’t the end of true love. When Sam (Patrick Swayze) is murdered during a mugging, his soul is trapped on Earth—which is how he discovers that his best friend is behind his death, and is already making moves on his girlfriend, Molly (Demi Moore). Sam soon enlists a psychic (Oscar-winner Whoopi Goldberg) to help him safe Molly from peril.
Call Me by Your Name
Timothée Chalamet plays the precocious Elio, a teenager living in Italy who becomes infatuated with an older American student, Oliver (Armie Hammer), who is staying with his family for the summer. What begins as a contentious friendship turns into a full-blown love affair as the two young men spend their idle summer days in the lush Mediterranean locale, bracing themselves for an inevitable heartbreak.
The Wedding Singer
Four Weddings and a Funeral
Pretty Woman
A Star Is Born
The classic Hollywood love story gets yet another modern musical spin, this time with first-time director Bradley Cooper starring as washed-up country singer Jackson Maine, whose life is given a boost when he falls for an aspiring pop singer, Ally (Lady Gaga). But as Ally’s star rises and Jackson’s falls, their rocky relationship is put to the test.
Hilary Weaver is a freelance writer based in New York who writes about politics, queer issues, Meryl Streep, Glenn Close, and every woman the Queen has ever made a dame.
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