History’s most iconic romances live forever on the silver screen, and whether you’re feeling hopeful or hopeless on this Valentine’s Day, settling in with a great rom-com is never a bad idea. To mark this Valentine’s Day weekend, we’ve assembled a list of the best romantic comedies on streaming – from tried-and-true classics to underrated gems. You’ll find swoon-worth couples like Julia Roberts and Hugh Grant, Meg Ryan and Tom Hanks and Heath Ledger and Julia Stiles on this list, plus many more.
So grab the chocolates, pop the popcorn and check out the best rom-coms to stream for Valentine’s Day.
“10 Things I Hate About You”
Stream on Disney+
This 1999 classic features Heath Ledger serenading Julia Stiles with a stunning rendition of “Can’t Take My Eyes Off of You,” a great soundtrack, Julia Stiles being a “heinous bitch,” three happily matched couples and a bully who finally gets the punch to the nose he so richly deserves.
“When Harry Met Sally”
Stream on Paramount+
A tried-and-true icon of the rom-com genre, “When Harry Met Sally” is maybe the best “friends-to-lovers” movie ever made. Meg Ryan and Billy Crystal are best pals who stay close over the years and through various other relationships. When will they finally admit they’re in love with each other? On New Year’s Eve, of course. The combo of director Rob Reiner (who had just gone through a divorce) and writer Nora Eprhon (a romantic) is dynamite, and the film boasts one of Carrie Fisher’s best roles.
“You’ve Got Mail”
Stream on Hulu
Nora Ephron’s 1998 film “You’ve Got Mail” is like a warm blanket. The second team-up between Meg Ryan and Tom Hanks, the story follows a small bookstore owner (Ryan) and the heir to a conglomerate book chain (Hanks) who hate each other in person, but – unbeknownst to each other – fall in love online anonymously as they begin chatting over the World Wide Web. A delight!
“How Stella Got Her Groove Back”
Stream on Hulu
Angela Bassett is killer in this 1998 film about a successful single parent who takes a vacation to Jamaica with her girlfriends and falls in love. But the film extends beyond simple rom-com trappings to basically stand as a chronicle of life at 40, and is all the better for it. Taye Diggs, Whoopi Goldberg and Regina King co-star.
“His Girl Friday”
Stream on Prime Video
If you thought the characters talked fast on “Gilmore Girls,” brother, have we got a movie for you: Cary Grant and Rosalind Russell play formerly married reporters who can’t resist a good scoop. Russell is supposed to be getting married to ho-hum Ralph Bellamy but who can resist Grant’s charms, even when he’s at his most high-handed? Essential viewing for cinephiles and anyone who needs convincing that black-and-white movies aren’t boring.
“Four Weddings and a Funeral”
Stream on Prime Video
Unique in structure and heavy on laughs and tears, “Four Weddings and a Funeral” follows a group of friends – including a budding relationship between Hugh Grant and Andie Macdowell – over the course of four weddings and a funeral, set primarily during these events. The film hails from “Love Actually” scribe Richard Curtis and helped launch Grant’s career.
“Notting Hill”
Stream on Netflix
Speaking of Hugh Grant, “Notting Hill” is a charmer. He plays a bookshop owner in Notting Hill, London who falls in love with an American movie star, played by Julia Roberts, when she steps in to buy a book. You know the line – “I’m just a girl, standing in front of a boy, asking him to love her.”
“To All the Boys I’ve Loved Before”
Stream on Netflix
If it’s YA romance you’re looking for, look no further than “To All the Boys I’ve Loved Before.” Laura Jean, a high school junior, writes private letters to her crushes just to get her feelings out. But when her sister actually mails the letters, suddenly her feelings are out in the open. That’s the set-up for this Jenny Han adaptation, but the resulting film is delightfully substantial, with winning performances from Lana Condor and Noah Centineo. It’s cute and sweet and swoon-worthy, and it kicks off a whole trilogy of films that are all streaming on Netflix.
“Hit Man”
Stream on Netflix
Glenn Powell and Adria Arjona are one of the most smoking hot screen couples of all time in Richard Linklater’s hilarious comedy. Powell is a delight as a mild-mannered techie who blossoms when he’s handed the job of playing a fake hit man for hire. Loosely based on a real story, but we doubt the “real” fake hitman had this much fun.
“Palm Springs”
Stream on Hulu
If goofy rom-coms are more your speed, “Palm Springs” will hit the spot. Part of the fun of this movie is not knowing what will happen next, but the basic premise is this: Andy Samberg is caught in a time loop, reliving the same day over and over again. That day just so happens to be a wedding in Palm Springs (not his), but when a bridesmaid (played by Cristin Milioti) gets stuck in the same time loop, suddenly these two individuals are stuck reliving the same day together. Will they? Won’t they? Will they get out? Find out in this hilarious and surprising comedy.
“Fire Island”
Stream on Hulu
Filmmaker Andrew Ahn’s 2022 film “Fire Island” is an inspired twist on “Pride and Prejudice” that follows a group of gay friends on vacation who struggle when sparks fly. Joel Kim Booster is the Elizabeth Bennett stand-in, Conrad Ricamora is Mr. Darcy and the ensemble includes Bowen Yang, Margaret Cho and Matt Rogers.
“Forgetting Sarah Marshall”
Stream on Max
So maybe you’re single? In that case, “Forgetting Sarah Marshall” – one of the ultimate break-up movies – will do the trick. Inspired by an incident in his own life, Jason Segel wrote and stars in this film about a guy going through a breakup with a famous actress (Kristen Bell as the titular Sarah Marshall) who decides to take a vacation to Hawaii, only to run into his ex who’s now vacationing with her new beau (Russell Brand). He strikes up a friendship with a local (Mila Kunis) while he tries to work out his feelings. Super funny, super sweet, this is top tier from the crop of Judd Apatow-produced comedies in the 2000s.
“Sixteen Candles”
Stream on Netflix
You can’t have a rom-com list without a John Hughes movie, and 1984’s “Sixteen Candles” is a swell pick for Valentine’s Day. Molly Ringwald stars as a high schooler turning 16 who is dismayed that her family forgot her birthday, agonizing over her crush on the hunky Jake and fending off advances from dorky freshman Ted (Anthony Michael Hall).
“50 First Dates”
Stream on Prime Video
Maybe Adam Sandler’s best comedy, “50 First Dates” is a lovely twist on romance. Sandler plays a marine veterinarian living in Hawaii who falls in love with an art teacher named Lucy (Drew Barrymore). Unfortunately, Lucy suffers short-term memory loss and can’t remember anything from the day before. Thus a romance blossoms in which Sandler’s character has to woo Lucy anew every day.
“13 Going on 30”
Stream on Netflix
Unendingly sweet, “13 Going on 30” follows a 13-year-old who wishes to be 30, only for her dream to come true – she awakes to find herself a successful 30-year-old, albeit the life and career she’s built for herself are a far cry from what she envisioned when she was a child. It’s “Big,” basically, but Jennifer Garner is a blast and Mark Ruffalo is tremendous as a romantic lead. Plus there’s a dance break to “Thriller.”
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