20 Best Romantic Movies of All Time to Watch on Valentine’s Day 2025

Don't you just love love?

written by Eavesdroppr's
19 min read
13 Feb, 2025

Romance Movies To Watch

Romantic movies, whether you love them or love them, are pure magic for the soul. With Valentine’s Day right around the corner, it’s the perfect time to indulge in the ultimate feel-good, heart-fluttering cinematic experiences. Whether you’re happily single, cozied up with a partner, or celebrating Galentine's with your besties, this list has something for you.

There’s nothing quite like a great romantic movie to set you up in a Valentine’s Day mood. For this list, we’ve handpicked the absolute best, and trust us, because we’ve seen them all and loved them all. From childhood friends-to-lovers tropes (Love & Basketball) to meet-cute romances (Love at First Sight), and even those messy-but-irresistible love triangles (Bridget Jones’s Diary), there’s something for everyone. Here are 20 best romantic movies of all time to watch on Valentine's day.

1. Serendipity (2001)

A true meet-cute classic! Serendipity is a beautiful movie that follows Jonathan (John Cusack) and Sara (Kate Beckinsale) who meet one fateful night but decide to leave their future up to fate. Years later, they’re both in serious relationships, yet can’t shake the feeling that destiny might still have plans for them, so they decide to do the craziest thing ever; search for each other.

2. Love at First Sight (2023)

This swoon-worthy Netflix gem follows two strangers who meet on a flight to London, only to be separated by fate. With a mix of charming performances by Haley Lu Richardson and Ben Hardy and another sprinkle of serendipity, Love At First Sight is an absolute must-watch for everyone.

3. Love & Basketball (2000)

A love story that spans childhood, adolescence, and adulthood, Love & Basketball follows Monica (Sanaa Lathan) and Quincy (Omar Epps), two aspiring basketball players whose love for the game and each other is tested over the years.

4. The Photograph (2020)

The Photograph stars Issa Rae and LaKeith Stanfield who bring this soulful romance to life. When Mae discovers a mysterious photograph in her late mother’s belongings, she embarks on a journey that leads her to Michael, starting a love story filled with passion and self-discovery, and a plot twist of distance attempting to pull them apart.

5. The Sun Is Also a Star (2019)

Based on the novel the Sun Is Also A Star by Nicola Yoon, this heartwarming movie follows Natasha (Yara Shahidi), a Jamaican immigrant facing deportation, and Daniel (Charles Melton), a poetic dreamer who believes in fate. Their whirlwind 24-hour romance is beautifully emotional, that is until real life and all it's hard circumstances happens.

6. When We First Met (2018)

Ever wished you could go back and redo the night you met your crush? That’s exactly what Noah (Adam Devine) does in this time-travel rom-com, trying over and over to win the girl of his dreams. When We First Met is a romantic story with a fresh twist that will make it even more interesting to watch.

7. I Hate Valentine’s Day (2009)

If you think you hate Valentine’s Day, watching I Hate Valentine's Day might just change your mind. Nia Vardalos stars as Genevieve, a florist who believes in a strict five-date rule, that is until she meets Greg (John Corbett) and starts reconsidering her rules. It is a movie that can turn a cynic into a lover.

8. Valentine’s Day (2010)

Valentine's Day has a star-studded cast with a love story that features multiple interwoven love stories in the days leading up to Valentine’s Day. With an all-star cast including Julia Roberts, Ashton Kutcher, and Anne Hathaway, Taylor Swift and an undeniable storyline that make this movie beautiful to experience.

9. Say Anything (1989)

Cue the boombox moment! Lloyd Dobler (John Cusack) is the ultimate romantic underdog in Say Anything, proving that persistence and grand gestures (like blasting music outside someone’s window) can still make hearts swoon.

10. 27 Dresses (2008)

27 Dresses is classic rom-com with a side of wedding chaos. Jane (Katherine Heigl) has been a bridesmaid 27 times but never a bride, until an unexpected romance with a cynical journalist (James Marsden) shakes things up. This movie has everything, from a "Bennie and the Jets" bar duet between Katherine Heigl and James Marsden that will stay on your mind forever, to a love story between the main characters that will melt your heart.

11. Bridget Jones’s Diary (2001)

Bridget Jones's Diary is an undeniably good romantic comedy that was way ahead of its time and also a classic. If you’re single and feeling some type of way about Valentine’s Day, Bridget (Renée Zellweger) is your spirit animal. Between Mark Darcy (Colin Firth) and Daniel Cleaver (Hugh Grant), this love triangle is deliciously chaotic.

12. The Other Zoey (2023)

The Other Zoey is a cute, modern twist on mistaken identity and unexpected love, this rom-com follows a girl who finds herself caught between her longtime crush and a guy who thinks she’s his girlfriend. Drew Starkey and Josephine Langford are the perfect duo in this romantic movie you'll love.

13. He’s Just Not That Into You (2009)

This rom-com gives a brutally honest yet hilarious take on modern dating. He's Just Not That Into You is a full fledged look inside the minds of men, it comes with relatable storylines and a fantastic cast, and it’s the perfect watch for anyone questioning love for women wondering how to know if he's into them.

14. Something Borrowed (2011)

It’s complicated, but in the best way. Rachel (Ginnifer Goodwin) realizes she’s in love with her best friend’s fiancé, and things get messy. With Kate Hudson, Colin Egglesfield, and John Krasinski, Something Borrowed will have you rooting for a love you maybe shouldn’t be rooting for.

15. You’ve Got Mail (1998)

You've Got Mail is a digital-age romance before online dating took over, it is a charming love story between rival bookstore owners (Tom Hanks and Meg Ryan), the story is timeless, beautiful and cozy.

16. Never Been Kissed (1999)

Never Been Kissed stars Drew Barrymore as a journalist who goes undercover in high school and unexpectedly finds romance in the wrong and the right place, and also in the most awkward ways possible. Sweet, funny, and nostalgic, it’s a total feel-good film that will make you want love till you go out there and get it.

17. Ella Enchanted (2004)

Ella Enchanted is a fairytale with a feminist twist! Ella (Anne Hathaway) is cursed to obey every command, but she fights back against fate while falling for a charming prince (Hugh Dancy). It's a light hearted period and fantasy themed film with magic, giants, elves, and the magic of love all rolled into one.

18. Enchanted (2007)

In Enchanted, Disney meets real-world romance in this magical film where a fairytale princess (Amy Adams) finds herself in modern-day New York and discovers that true love isn’t always what she expected, there's singing and Patrick Dempsey.

19. Letters to Juliet (2010)

When Sophie (Amanda Seyfried) discovers a decades-old love letter in Verona, she embarks on a journey to reunite lost lovers and maybe find love herself. Letters to Juliet is a feel-good romance that makes people believers in love because of how good it is

20. Win a Date with Tad Hamilton! (2004)

Win a Date With Tad Hamilton is one of those movies that is worthy of your time. In this romantic comedy, a small-town girl (Kate Bosworth) wins a date with a Hollywood heartthrob (Josh Duhamel), but real love might be closer than she thinks.