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The Best Valentine’s Day Movies, Even if You Hate Valentine’s Day

Love is in the air. And, like it or not, Hallmark has declared February 14th the most romantic day of the year, and Hollywood has seen fit to jump on that sugar-coated, flower-filled bandwagon.

Thing is, Valentine’s Day doesn’t have to be the most depressing day of the year (even if your idea of a candlelit V-Day dinner includes a bowl of raw cookie dough and your dog). There are plenty of great films out there for the lover in all of us, regardless of whether or not we’re doomed to spend eternity alone, surrounded by stacks of newspapers from 1993.

These are not your typical rom-coms — okay, so maybe some of them fall into that category — but the thing about these movies is that they’re totally lovable, even if you happen to hate February 14th with a fiery, soul-crushing passion.


Ah, the lengths that one would go to for true love. The Princess Bride is, on the surface, a charming fairytale about a hero who rescues a beautiful princess from an evil villain. But toss in a good bit of humor (what’s up, Billy Crystal), an epic battle of wits, and a sweet story shared between a boy and his grandfather, and you’ve got a classic film that’s watchable on any day of the year.

Starring Cary Elwes,  Mandy Patinkin, and Robin Wright

Directed by Rob Reiner


Set in the mid-’80s, The Wedding Singer follows the meant-to-be relationship between wedding singer Robbie and waitress Julia, who both happen to be engaged to different people. It’s probably the best of Sandler’s and Barrymore’s on-screen pairings, and it’ll make you feel nostalgic for the decade of big hair and new wave radio, even if you were born well after the fact.

Starring Adam Sandler and Drew Barrymore

Directed by Frank Coraci


Scott Pilgrim is one of the most unlikely romantic leads you’ll ever see in a movie, and his epic quest to win the heart of his beloved Ramona winds up leading to one of the most unlikely romantic comedies of the 2000s. It’s less of a rom-com and more of a flashy, balls-out, video game adventure, which is why it’s a great choice for those of us who celebrate love a little differently than our parents did.

Starring Michael Cera, Mary Elizabeth Winstead, and Kieran Culkin

Directed by Edgar Wright


Annie Hall is the story of the on again/off again relationship between New York writer Alvy Singer and aspiring actress/singer Annie Hall. It’s arguably one of Woody Allen’s greatest films, which finds its place somewhere between awkward neuroses, true love, and the hard realization that sometimes true love just isn’t viable in the real world.

Starring Woody Allen and Diane Keaton

Directed by Woody Allen


Sometimes, love happens when you’re 15. Sometimes, it doesn’t. For Andy, finding that special someone just sort of takes longer than most. The 40-Year-Old Virgin is as hilarious as it is uncomfortable, and it’s sure to give you a new appreciation for those mint condition action figures your parents convinced you not to take out of the boxes.

Starring Steve Carell,  Catherine Keener, and Paul Rudd

Directed by Judd Apatow


When it comes to top romance films, Say Anything makes pretty much everyone’s list. And the image of underachiever Lloyd Dobler blasting Peter Gabriel’s “In Your Eyes” from a boombox will forever go down as one of the most romantic gestures in cinematic history. Plus, it’s John Cusack at his absolute best, so there’s really zero excuse to not watch it.

Starring John Cusack, Ione Skye, and John Mahoney

Directed by Cameron Crowe


If you hate love and romance (but also secretly love it), Eternal Sunshine of the Spotless Mind is the film for you. From the creative mind of Charlie Kaufman, the film takes place mostly in protagonist Joel’s memories as they’re systematically being erased, following his turbulent relationship and subsequent breakup with flighty Clementine. It’s cerebral and sad and sweet, and it’s a completely different take on the genre.

Starring Jim Carrey and Kate Winslet

Directed by Michel Gondry


Struggling musician Peter Bretter takes a trip to Hawaii as a last-ditch effort to get over his ex, TV star Sarah Marshall, only to discover he’s sharing the same hotel as she and her new douchey boyfriend are. Jason Segel plays heartbreak with hilarious sensitivity, and it ends with a puppet musical, which means the film definitely has a little something for everyone.

Starring Kristen Bell,  Jason Segel, and Paul Rudd

Directed by Nicholas Stoller


Reality Bites has made its mark as one of the most prominent “Gen-X” films of the ’90s, and, surprisingly, still holds up. It deals mostly with the disillusionment of the post-grad crowd — that, just because you have a degree doesn’t mean your life immediately has purpose, feeling that so many of us have experienced these days. But there’s also a heartfelt love story thrown in amid the production of a documentary, so we’re going to count it.

Starring Winona Ryder,  Ethan Hawke, and Janeane Garofalo

Directed by Ben Stiller


The first film in Richard Linklater’s Before trilogy, Before Sunrise is the story of two people who meet on a train in Europe and wind up spending a single, life-changing night together. It’s hands down one of the most romantic films ever made, so if you’re one of those non-believers, this one might just actually change your mind.

Starring Ethan Hawke and Julie Delpy

Directed by Richard Linklater