It doesn’t require a deep dive into the history of Valentine’s Day to understand just how alienating it can be for some people. Whether you’re single or you’ve found your soul mate, one of the best ways to find a spark of romance is to find some great at-home entertainment. Of course, if you do have a partner, you might want to also check out these Valentine’s Day gifts for men, or maybe even look into a last-minute flower delivery. These gestures are great, but for plenty of people, a great movie is the best way to find some romance.
Watching Valentine’s Day movies, or romantic movies more generally, is nothing to be ashamed of. These movies are designed to make you think about love, which is one of the most powerful emotions we can feel. If you find yourself weeping softly into your assembled Valentine’s Day chocolates over this list of movies, don’t sweat it. Love hurts, no matter who you are.
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The Wedding Singer (1998)
100m
Genre
Romance, Comedy
Stars
Adam Sandler, Drew Barrymore, Christine Taylor
Directed by
Frank Coraci
Watch on Amazon
One of the better Adam Sandler movies of our generation, The Wedding Singer is a genuine and sweet story about how hard it can be to believe in true love. When a low-income wedding singer is left at the altar by what he thinks is the love of his life, he must put the pieces of his heart back together. Luckily, he meets the charming Julia Sullivan (Drew Barrymore) who makes the process much easier. Full of the classic Sandler movie cameos and silly songs, this is a feel-good movie that will have your partner asking, “When are you going to do that for me?”
Shakespeare in Love (1998)
123m
Genre
Romance, History, Comedy
Stars
Joseph Fiennes, Gwyneth Paltrow, Geoffrey Rush
Directed by
John Madden
Watch on Paramount+
Wise and witty, Shakespeare in Love is just the right mix of head and heart. Following a young and uninspired William Shakespeare (Joseph Fiennes) who is having a major writers block and failing to meet basically any of his obligations, until he meets a young and rebellious Viola (Gwyneth Paltrow) who poses as a man to audition for one of his plays. Providing more than just romance, this classic ode to the Elizabethan Era is a potent mix of suspense, comedy, and utmost passion for theater.
Definitely, Maybe (2008)
112m
Genre
Comedy, Romance
Stars
Ryan Reynolds, Abigail Breslin, Elizabeth Banks
Directed by
Adam Brooks
Watch on Amazon
Maybe one of the best classic rom-coms out there, Definitely Maybe is a touching story with an all-star cast that also gets some points for creativity. The film explores the love life of an almost-divorced Ryan Reynolds as he explains to his daughter (Abigail Breslin) how he and her mom met, omitting the real names of his past lovers in the story so she can guess which one is her mom. This movie is full of sympathetic moments of intimacy and vulnerability, and a number of great performances. We wouldn’t call this a typical Reynolds role, but it’s one of the best Ryan Reynolds movies for sure.
Romeo + Juliet (1996)
120m
Genre
Drama, Romance
Stars
Leonardo DiCaprio, Claire Danes, Jesse Bradford
Directed by
Baz Luhrmann
Watch on HBO Max
Another Shakespearean addition to this list, Romeo + Juliet is a masterful rendition of the age-old tale, made epically offbeat and glamorous by Baz Luhrmann. Keeping the script exactly the same, Romeo (Leonardo DiCaprio) and Juliet (Claire Danes) meet in a modern-day (well, the 90s) Verona, where the Montagues and Capulets face-off with stylish, customized handguns to replace the elegant blades of days long gone. Complete with a contemporary, cutting soundtrack and a glorious cast, Romeo + Juliet remains one of the most successful Shakespeare adaptations ever produced.
10 Things I Hate About You (1999)
97m
Genre
Comedy, Romance, Drama
Stars
Julia Stiles, Heath Ledger, Joseph Gordon-Levitt
Directed by
Gil Junger
Watch on Disney+
With a story based on Shakespeare’s The Taming of the Shrew and re-vamped to fit the 90s grunge of Seattle, 10 Things I Hate About You is a timeless classic, and one of the best high school rom-coms. In an upper-middle-class Seattle high school, Bianca (Larisa Oleynik) is a popular and beautiful girl that many would feel lucky to date (arrogant schmucks and romantic nerds alike), but with her terrified and controlling father, she is not allowed to date unless her blunt and abrasive older sister, Kat (Julia Stiles) decides to date somebody first. Starring a wide array of recognizable faces, 10 Things charms from front to back, and at least one viewer will fall victim to Heath Ledger’s endlessly charming smile.
Always Be My Maybe (2019)
102m
Genre
Romance, Comedy
Stars
Ali Wong, Randall Park, Keanu Reeves
Directed by
Nahnatchka Khan
Watch on Netflix
If you’re looking for a good romantic comedy on Netflix, Always Be My Maybe is a great place to start. The story follows Sasha (Ali Wong) and Marcus (Randall Park), two people who everyone assumed would end up together. After reconnecting after 15 years apart, they begin to think they might be meant to be. Oh, and Keanu Reeves shows up for a great extended cameo.
Moulin Rouge! (2001)
128m
Genre
Drama, Romance, Music
Stars
Nicole Kidman, Ewan McGregor, John Leguizamo
Directed by
Baz Luhrmann
Watch on Amazon
Moulin Rouge! is a glorious spectacle of musical talent and romantic tragedy. A penniless poet (Ewan McGregor) begins to fall in love with a lovely, sultry, courtesan singer (Nicole Kidman), whose hand has been promised to a duke in order to fund the next big production at the Moulin Rouge. With surprising musical performances of contemporary classics from McGregor and Kidman and visceral scenes of emotional distress highlighted by extreme color schemes, this musical is unlike any other.
The Big Sick (2017)
120m
Genre
Comedy, Drama, Romance
Stars
Kumail Nanjiani, Zoe Kazan, Holly Hunter
Directed by
Michael Showalter
Watch on Amazon
The Big Sick is based on the real-life love story of comedian Kumail Nanjiani and Emily V. Gordon. The story follows Nanjiani as he struggles to build up a career in stand-up. After a run-in with a heckler named Emily (Zoe Kazan), the two quickly form a relationship. However, the couple is faced with a family pushback and when they break up, Emily falls into a coma that eventually brings them back together. This original dramedy is one of the best movies Amazon Prime has to offer.
50 First Dates (2004)
99m
Genre
Comedy, Romance
Stars
Adam Sandler, Drew Barrymore, Rob Schneider
Directed by
Peter Segal
Watch on Peacock
Another Adam Sandler rom-com, also featuring Drew Barrymore, 50 First Dates is a comical dramedy that gets pretty sad but also has some moments of wonderful devotion and love every couple should aspire to. The film follows Henry Roth, a ladies man who can’t commit who finally meets the girl of his dreams. Unfortunately, she turns out to have short-term memory loss, resetting the clock every day when she goes to sleep. Is it a little corny, sure? Even so, you’ll find yourself crying by the time the credits roll.
Lost in Translation (2003)
102m
Genre
Drama, Romance, Comedy
Stars
Bill Murray, Scarlett Johansson, Giovanni Ribisi
Directed by
Sofia Coppola
Watch on Amazon
Lost in Translation is a critically acclaimed masterpiece that plays out on a remarkably small scale. When a sad, lonely movie star (Bill Murray) serendipitously meets a newly married and skeptical young woman (Scarlett Johansson) in Tokyo, the chemistry is instant and their facades quickly fade. Fans of Murray’s work will undoubtedly enjoy this Sofia Coppola classic, which is about the kind of platonic, maybe romantic love that can exist between two people of any age.
Eternal Sunshine of the Spotless Mind (2004)
108m
Genre
Science Fiction, Drama, Romance
Stars
Jim Carrey, Kate Winslet, Kirsten Dunst
Directed by
Michel Gondry
Watch on Amazon
In a conceptual tour de force film, Eternal Sunshine of the Spotless Mind manages to challenge your very notions of what memory is for. Joel (Jim Carrey) is on a train for his usual commute when he meets Clementine (Kate Winslet), a quirky, overtly forward individual who makes outrageous statements that catch our protagonist’s ear. When their relationship gets nasty, they individually seek out the help of an experimental memory-removal clinic that reminds them exactly why they belong together. This is a fantastic love story and arguably one of the best Jim Carrey movies ever.
