What to Watch on Valentine’s Day, Regardless of Your Feelings About Them
With these vintage films, you can take a break from reality for a while.
In our minds, there are two types of Valentine’s Day movie adventures that we associate with the holiday. Either you’re out on a romantic date with your sweetheart, or you’re cozying up in a theater seat before heading out to a candlelit supper after the show. In the other scenario, you’re slouched in bed alone, sipping cocktails and wishing the couples on your television screen ill. However, even the most corny rom-coms of days could arguably offer a more nuanced perspective on love, even if they are perfectly valid ways to commemorate St. Valentine’s Day.
The truth is that love comes in many forms, from friendship to romance to self-love, and everything in between. And it’s reflected in our history of romantic comedies, which have gradually replaced clichéd flings with more complex love stories that include representations of queer partnerships, odes to friendship, and more.
Whatever your relationship status is, there’s a strong possibility that you’ll discover a movie buddy this year. Totally smitten with someone? The Notebook or The Half of It are two examples of emotional movies that will make you feel better about yourself. No, I’m not married. Palm Springs will calm your cynical side, while She’s Gotta Have It will make you proud of your non-monogamy. Heartbroken? Let yourself be soothed by Call Me By Your Name and perhaps a phone call to a buddy.
The point is that there are a lot of fish to choose from. Here are a few picks that are sure to make your heart sing, your funny bone tingle, or your eyes water. Take a date, some sweets, or a group of close friends. This list includes some of the best Valentine’s Day movies ever made, in my opinion.
1. Always Be My Maybe
The reality that most couples who have been together since their adolescence have likely seen each other in their peak adolescent awkwardness is often overlooked in the “high school sweetheart” tale. Being there for someone even after they’ve done something terrible for you may be the ultimate test of a person’s love. As two former childhood friends reconnect in adulthood for the first time since their highly awkward coupling in their youth, Always Be My Maybe dives headfirst into the discomfort. It’s impossible not to fall in love with Ali Wong and Randall Park’s humorous and romantic connection when you see them together.
2. If Beale Street Could Talk
It’s based on James Baldwin’s 1974 novel If Beale Street Could Talk and directed by Moonlight’s Barry Jenkins, If Beale Street Could Talk tells the wonderful love tale of Tish and Fonny. When Fonny is wrongfully accused of a crime and imprisoned, their course changes. Prior to giving birth, Tish sets out to clear the name of her soon-to-be husband, Fonny. She narrates their narrative from the beginning. If Beale Street Could Talk, starring Kiki Layna, Stephan James, Regina King, and Colman Domingo, tells the story of a love that perseveres in the face of adversity.
3. The Half of It
It’s about time a movie like Alice Wu’s The Half of It appeared in the annals of the coming-of-age rom-com canon. Ellie Chu, a young bookworm, helps a high school athlete court his crush by composing love letters on his behalf in a Cyrano de Bergerac-esque love triangle. This realization that Ellie is in love with the same girl as everyone else leads to a heartwarming journey of love, self-acceptance, and maturation for Ellie.
4. Sylvie’s Love
In the 1960s, Harlem provides a magnificent setting for a melancholy “right location, wrong time” love story that will have you swooning. Robert, played by Nnamdi Asomugha, is a world-traveling musician when he meets Sylvie, played by Tessa Thompson, who is married to a guy serving in the Korean War. It wasn’t until years later that their paths crossed once again that they were finally able to explore the sentiments they had for one another.
5. Portrait of a Lady on Fire
Yearning is the perfect way to celebrate Valentine’s Day. Portrait of a Lady on Fire, on the other hand, is a masterclass in how to portray a subdued love story. Perhaps it’s time to put an end to the “forbidden love” era film in LGBT cinema. Even if there isn’t a lot of romance in the film, the cinematography and dialogue are both stunning. By the conclusion of your movie night, you’ll find yourself waxing lyrical about your significant other. Or, you know, crying in private. You may be going for a more spooky, ghoulish feel this year. We don’t make assumptions.
6. She’s Gotta Have It
One of Spike Lee’s greatest works (and the one that put him on the map). The story of a lady who refuses to settle for a relationship with just one man is told in this 1986 film about three men she dates simultaneously. As a woman, you realize you’ve got to live your own life. Even while it’s a fantastic Valentine’s Day movie since it tickles the romantic itch, it also pays a nod to people who prefer a more free-spirited way of existence.
7. Palm Springs
For those who have had enough of love, here’s one for you. Often, the best love stories come from a skeptic’s point of view. It’s Andy Samberg as a man who can’t get out of a time loop after a fateful wedding day and finds himself in a lonely existence… until he meets another person who also finds themselves in a time loop with him.
8. Sleepless in Seattle
To get a fresh start after the death of Maggie, Sam Baldwin and his son Jonah relocate from Chicago to Seattle. However, when 8-year-old Jonah discovers that his father, Sam (Tom Hanks), is still single, he decides to intervene in his father’s love life. Dr. Marcia, a prominent radio broadcaster, receives a call from him on Christmas Eve and informs her that his father has to find a new girlfriend. After a while, letters begin to arrive from all over the country, and one of them is sent by Annie Reed, a passionate Baltimore reporter. When they meet on Valentine’s Day this year, she wants them to meet in the Empire State Building, much like in the movie An Affair to Remember (1957). Real-life wife Rita Wilson of Tom Hanks appears in this film as well.
9. Someone Great
Gina Rodriguez stars in Someone Great, an almost anti-romantic comedy about friendship and love that slipped under the radar when it initially came out.
10. Love Simon
In Love, Simon, a high schooler who falls in love with an online suitor who is battling with his own sexuality narrates the story of how he tries to come out of the closet after falling in love with him.
Iconic Will Smith role: matchmaker who might use some of his own advice in Hitch.
12. The Bridges of Madison County
Even the hardest nut will cry at the end of this 1995 film starring Meryl Streep and Clint Eastwood. Adapted from the 1992 book of the same name, Francesca Johnson is a 1960s Italian-immigrant housewife in Iowa who falls in love with a National Geographic drifting photographer. Clint Eastwood, who played the dashing and mysterious Robert Kincaid from Washington state, also directed and starred in the film. A faint Iowan lilt in her Italian accent will make you want to give up trying because she’s already nailed it.
13. My Best Friend’s Wedding
To ensure that they would both be unmarried by the age of 28, Julianne Potter (Julia Roberts) and Michael O’Neal (Dermot Mulroney) made a bargain. Julianne learns about Michael’s engagement to Kimberly just four days before her 28th birthday (Cameron Diaz). By the time Julianne realizes that she doesn’t want Michael to get married to anybody but her, she has plotted a means to break it up. In this film, “I Say a Little Prayer” is sung with such fervor that it begs to be performed at weddings and rehearsal dinners alike.
14. The Big Sick
“The Notebook” tells the true story of how Kumail Nanjiani and Emily V. Gordon met and fell in love through their real-life story. The film stars Kumail Nanjiani as himself, and Zoe Kazan as Emily, who both in the film and in real life became suddenly ill shortly after she and Kumail called it quits on their relationship. Ray Romano and Holly Hunter play Emily’s parents, who fly in to take care of their daughter while she is in a hospital coma. Kumail, on the other hand, is still trying to convince Emily that he is the right guy for her.
15. Notting Hill
Julia Roberts has a reputation for being a master of the love story. Roberts plays Anna Scott, a famous actress who just wants a normal life, in this other beloved 1990s rom-com. He is Will Thacker, an awkward British bookshop proprietor in London’s Notting Hill district (Hugh Grant). A key problem for Will and Anna’s unique connection is that their lifestyles are so different.
16. 10 Things I Hate About You
Seattle grunge scene is a setting for a film based on William Shakespeare’s The Taming of the Shrew, which is set in late 1990s. When it comes to teens, Kat Stratford (Julia Stiles) doesn’t have a clue what they’re getting themselves into. Bianca (Larisa Oleynik), the younger sister, is dubbed “the shrew” because she wants to date, go out, and be a typical high schooler. Is there anything more I need to know? If Kat does not date Bianca, their father will not allow it. As a fresh student, Cameron (Joseph Gordon-Levitt) asks Patrick Verona to kill Kat so that he can pursue Bianca (Heather Ledger). A transaction like that, surely, could not go wrong?
17. Crazy, Stupid, Love
Emily Weaver (Julianne Moore) informs her husband Cal Weaver (Steve Carrell), her high school sweetheart and husband, that she wants a divorce. Then, Cal does a full Ladybird and leaps out of the car to express his displeasure with the situation. Jacob (Ryan Gosling), who finds Cal moping around a bar and decides to help him become a modern gentleman, shows up and turns things around for him. The first 15 minutes of the movie haven’t even shown yet, you jerks.
18. The Last Five Years
It’s a great time to be in your relationship. You’ll love this movie. Has your relationship reached its lowest point, or am I asking too much? This film is definitely for you, by the way. The only prerequisites for this picture are a fondness for the singing voices of Anna Kendrick and Jeremy Jordan and a passing familiarity with the concept of “love.” The rest of the album is a musical journey between two people telling their love story via song. It’s best to start at the beginning and work your way through the process. One begins at the end and works backwards.
19. While You Were Sleeping
For those who don’t celebrate Valentine’s Day, this film is a great choice for the holiday season. Transit worker Lucy Moderatz (Sandra Bullock) rescues her admirer Peter (Peter Gallagher) after he has fallen and hurt his head on the tracks in Chicago during the harsh winter. Even though Peter is in a coma, the rest of his family believes that he and Lucy are engaged. Lucy accepts Peter’s invitation to spend the holidays with Peter’s family, even though he doesn’t even know her name. Jack, Peter’s brother, becomes her new boyfriend while Peter is sleeping (Bill Pullman). This may seem like a lot to cover in a single film, but have faith that it will be worth your time.
Similarly to While You Were Sleeping, the story revolves around a woman who falls head over heels in love with her putative boyfriend’s brother. Widow She accepts Johnny (Danny Aiellomarriage )’s proposal but falls in love with his younger brother, Ronny (Cher) (Nicolas Cage). But this isn’t the only family hidden romance. For this role in 1988, Cher received an Oscar; it was the same year that she donned the infamous Bob Mackie gown.
21. When Harry Met Sally…
Even the most ardent rom-com hater succumbs to Rob Reiner’s modern masterpiece. Nora Ephron’s storyline and Billy Crystal and Meg Ryan’s contagious and wonderful chemistry make the film one of the greatest romantic comedies ever made.
22. You’ve Got Mail
Meg Ryan plays a Manhattan bookseller whose shop suffers when a big-box bookstore led by a cunning Tom Hanks enters into the area in Nora Ephron’s digital era adaptation of The Shop Around the Corner. But these enemies don’t realize that they’ve fallen in love while chatting anonymously over email.
23. Love & Basketball
Playing childhood sweethearts who simultaneously aim to be basketball stars, Omar Epps and Sanaa Lathan feature in this romantic comedy. In this romantic drama, written and directed by Gina Prince-Bythewood, the two protagonists must reconcile their objectives and feelings as they fall in love both on and off the court.
24. The Notebook
When two young lovers are unable to communicate their feelings to one other because of their social circles, but still find a way to convey their true love in this romantic tearjerker starring Ryan Gosling and Rachel McAdams (particularly by kissing a lot in the pouring rain).
One of the greatest romantic films ever created is the classic drama. At the height of World War II, former lovers Humphrey Bogart and Ingrid Bergman find themselves reuniting in Morocco, but their blissful reunion is soon shattered when the woman seeks Bogart’s assistance in escaping to the United States with her new husband.
26. Eternal Sunshine of the Spotless Mind
Both Jim Carrey and Kate Winslet play lovers who are heartbroken over the breakup of their relationship and decide to have each other erased from their minds. The procedure only serves to reignite their love for one another in Michel Gondry’s inventive and heartbreaking drama.
27. Crazy Rich Asians
He doesn’t know it yet, but Rachel Chu, Henry Golding’s onscreen love interest, is from a wealthy family in Asia. In Singapore, she’s confronted with his imposing and ferocious mother, whose demeanor is a stark contrast to her own (Michelle Yeoh).
28. Blue Is the Warmest Color
This romantic coming-of-age movie starring Léa Seydoux and Adèle Exarchopoulos, which was awarded the Palme d’Or at the Cannes Film Festival, will take you on an emotional roller coaster.
While James Cameron’s Academy Award-winning film boasts some impressive special effects work, the film also tells the narrative of a forbidden romance between a struggling artist (Leonardo DiCaprio) and an upper-class debutante (Kate Winslet) on board the tragically sinking RMS Titanic.
30. Love Story
Ali MacGraw and Ryan O’Neal starred in the film adaptation of Erich Segal’s best-selling novel, in which a young Harvard man falls in love with a working-class Radcliffe student. When she is diagnosed with a fatal disease, their relationship is put to the test in the most typical weepy way possible.