Valentine’s Day is the perfect excuse to curl up with your favorite snacks, grab a cozy blanket, and indulge in a rom-com marathon. Whether watching with your besties or your partner, or just enjoying a solo self-care night, these movies will bring on the laughs, the swoons, and all the feel-good vibes. Here’s my ranking of the ultimate must-watch romantic comedies.
1. When Harry Met Sally (1989)
Storyline: Harry and Sally first meet during a long road trip to New York, where they debate whether men and women can ever be friends. Over the years, their paths continue to cross, and their friendship grows—until it inevitably turns into something more complicated.
Why It’s a Must-Watch: This classic rom-com sets the gold standard for the genre with its witty dialogue and endearing performances by Billy Crystal and Meg Ryan. With the ultimate debate: can men and women really be friends? It’s smart, heartwarming, and features that iconic diner scene.
2. 10 Things I Hate About You (1999)
Storyline: High school bad boy Patrick Verona (Heath Ledger) is paid to take out the sharp-tongued, independent Kat Stratford (Julia Stiles) so her younger sister can start dating. But what starts as a setup turns into a real romance, leading to one of the most iconic teen rom-com moments—Patrick’s serenade of Can’t Take My Eyes Off You.
Why It’s a Must-Watch: A modern retelling of The Taming of the Shrew, this film delivers charm, sarcasm, and Heath Ledger’s swoon-worthy performance. With its mix of romance and rebellion, it’s the perfect throwback for your Valentine’s lineup.
3. Crazy, Stupid, Love (2011)
Storyline: Middle-aged Cal Weaver (Steve Carell) is heartbroken after his wife leaves him, but his love life takes an unexpected turn when he meets ladies’ man Jacob Palmer (Ryan Gosling), who teaches him how to win women over. Meanwhile, Jacob’s life gets flipped upside down when he falls for quirky but charming Hannah (Emma Stone).
Why It’s a Must-Watch: Featuring an all-star cast, this movie blends humor, romance, and unexpected twists. Plus, Ryan Gosling’s Dirty Dancing lift scene? Iconic.
4. How to Lose a Guy in 10 Days (2003)
Storyline: Andie Anderson (Kate Hudson), a magazine writer, is on a mission to drive a man away in ten days for a story, while Benjamin Barry (Matthew McConaughey) bets that he can make any woman fall in love with him in the same time frame. The result? Chaos, laughter, and some truly unforgettable romantic moments.
Why It’s a Must-Watch: Kate Hudson and Matthew McConaughey have electric chemistry in this hilarious battle-of-the-sexes rom-com. Between the over-the-top antics and undeniable charm, it’s a Valentine’s Day essential.
5. Legally Blonde (2001)
Storyline: Elle Woods (Reese Witherspoon) follows her ex-boyfriend to Harvard Law School in an attempt to win him back, only to end up being a better lawyer than him.
Why It’s a Must-Watch: While not a traditional rom-com, Elle Woods’ journey of self-love and success—while proving she’s so much more than just a pretty face—makes this a top-tier feel-good movie with a romantic subplot.
6. The Proposal (2009)
Storyline: High-powered editor Margaret Tate (Sandra Bullock) forces her assistant, Andrew Paxton (Ryan Reynolds), into a fake engagement to avoid deportation. A trip to his eccentric family in Alaska, however, makes their charade much more complicated—and unexpectedly real.
Why It’s a Must-Watch: Sandra Bullock and Ryan Reynolds bring the laughs and the sparks in this hilarious fake-relationship rom-com. Watching their chemistry unfold (plus that unexpected strip-dance scene) makes this one unforgettable.
7. Monte Carlo (2011)
Storyline: After graduating from high school, Grace (Selena Gomez) and two friends embark on their dream trip to Paris. However, when Grace is mistakenly identified as a British socialite named Cordelia, she decides to pretend to be her. This allows Grace and her friends to head to Monte Carlo, where they enjoy a week filled with yacht parties and charming bachelors—at least until the real Cordelia arrives.
Why It’s a Must-Watch: This movie is perfect for anyone who loves travel, mistaken identities, and fairytale-like romances. Plus, Selena Gomez shines in a double role, bringing both charm and humor to this underrated gem.
8. To All the Boys I’ve Loved Before (2018)
Storyline: Lara Jean Covey’s (Lana Condor) secret love letters to all her past crushes are accidentally sent out, leading to a fake dating scheme with popular heartthrob Peter Kavinsky (Noah Centineo). What starts as pretend quickly turns into something real.
Why It’s a Must-Watch: This Netflix hit perfectly captures young love, thanks to Lara Jean’s relatable charm and Peter Kavinsky’s heart-melting moments. It’s a modern rom-com classic for the hopeless romantics.
9. Love Actually (2003)
Storyline: A heartwarming collection of interwoven love stories that take place during the holiday season, following a variety of characters as they navigate romance, heartbreak, and grand gestures of love.
Why It’s a Must-Watch: This holiday-adjacent rom-com is packed with multiple love stories, making it perfect for any romantic occasion. With a mix of humor, heartbreak, and memorable moments (hello, cue cards scene!), it’s an emotional rollercoaster worth watching.
10. Notting Hill (1999)
Storyline: Ordinary bookstore owner William Thacker (Hugh Grant) has his world turned upside down when world-famous actress Anna Scott (Julia Roberts) walks into his shop. Their romance is tested by the pressures of fame and the everyday struggles of love.
Why It’s a Must-Watch: Julia Roberts and Hugh Grant deliver timeless performances, and the dreamy romance paired with the unforgettable “I’m just a girl, standing in front of a boy” line make this one of the most heartfelt rom-coms ever.
No matter your relationship status, these rom-coms are guaranteed to make your Valentine’s Day extra special. From timeless classics to modern gems, this list has something for every type of romantic. So grab some chocolate, hit play, and enjoy the ultimate love-filled movie night!