14 Romantic Films for Valentine’s Day (that Guys Will Like)

Movies Lists Valentine's Day
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It’s a common misconception that male viewers aren’t interested in great film romances. But just because premises involving Katherine Heigl as a saucy bounty hunter fail to generate considerable enthusiasm in the male demographic, that doesn’t mean the more bellicose sex is completely cold and unfeeling.

Valentine’s Day, for all its pageantry and commercialism, is always a good time of year to revisit some of the great films out there with a primarily romantic bent. Some of these are more comedy than romance, and others have sci-fi, musical or sports-related twists, but every one of them is an excellent film in its own right that your boyfriend, husband or otherwise male object of interest probably wouldn’t mind watching this Valentine’s Day.


1. Groundhog Day (1993)
Everyone loves Groundhog Day, right? I’ve always found it curious that many people don’t regard it primarily as a romance. I guess it’s understandable given how funny it is and its fantastical premise, but much of this story is about Bill Murray’s character learning how to truly love someone other than himself. He develops such a profound longing over time for Andie MacDowell’s character because he’s given unlimited time to fully appreciate what makes her unique, which transforms his baser lusts into genuine love. Ultimately, he works toward making her life better in the one day he’s allotted with a selflessness that comes from a lack of expectations of reward.


2. It Happened One Night (1934)
Valentine’s Day is a great opportunity to revisit some film classics from the Golden Age of Hollywood, and they don’t come any more classic than It Happened One Night. In many ways the quintessential American romantic comedy to predate the implementation of the Production Code in 1934, it tells the story of a young socialite runaway (Claudette Colbert) who tags along with a streetwise reporter (Clark Gable). It goes pretty much exactly as you’d expect—they both learn from each other’s very different skill set, and opposites absolutely attract. It’s famous for its hitchhiking scene, where the wily Colbert successfully flags down a car simply by showing a little leg, completely emasculating Gable. His reaction is priceless.


3. Moonrise Kingdom (2012)
Wes Anderson’s 2012 film is described as an “eccentric pubescent love story,” but it’s really not quite as eccentric as it would have you believe. Through just about any form of measurement, it’s probably Anderson’s most simple and sincere film, a genuinely heartfelt story about a couple of weird kids and their confusing adolescent romance. The director’s films are so often about exceptional children growing into adults who fail to achieve their promise, but here they never have that chance. It’s an optimistic story that entertains the possibility that maybe love really is all we need. Call it sappy, but the innocence is refreshing. Also, Billy Murray is there—perhaps his presence is the biggest deciding factor to getting on this list?


4. Drinking Buddies (2013)
If you feel compelled to go full indie and can’t stand love stories with tidy, happy endings, Drinking Buddies should be your pick. It’s an unconventional romance in that most of the characters never commit to the relationships or infidelities we expect them to. Instead, it’s about temptation, the lies we tell ourselves in a relationship and the boundaries between friendship and romantic feelings. A scion of but not full-fledged entry into the mumblecore genre, its largely improvised dialog lends an air of reality to the conversations, but those expecting typical genre conventions may find themselves perplexed when you don’t get anything resembling the “wedding bells” ending of the typical romantic comedy.


5. Waitress (2007)
A comedy drama starring Keri Russell as a pie-baking waitress probably doesn’t sound like something your boyfriend would seek out, but Waitress is much more than meets the eye. A fun, quirky movie that’s as emotionally affecting as it is entertaining, it plays like a more feminine Coen Brothers flick. Russell is wonderful as Jenna, a Southerner waitress who finds empowerment and freedom from her overbearing, emotionally abusive husband first in an affair and then in a new source of love. This film, unlike some of the others, is not so much about romantic love as it is about finding love for self. It was an impressive achievement for writer/director Adrienne Shelly, who was tragically murdered three months before its debut.


6. Scott Pilgrim vs. the World (2010)
I love Edgar Wright’s whole “Cornetto trilogy” of Shaun of the Dead, Hot Fuzz and The World’s End, but for my money this is easily his most impressive film to date. For all the appreciation that has grown for it since its poor box office showing, Scott Pilgrim still hasn’t truly gotten its due. Most of what makes it great (in addition to the stellar writing) is Wright’s incredibly creative visual aesthetic, seamlessly blending influences from comics, video games and pop art into a whole that just works, against all odds. The romance aspect is a bit more “young adult” and inconsequential, but you’re unlikely to notice in a film so vibrant and full of life.


7. His Girl Friday (1940)
If you’ve ever wondered “what the big deal” is about women and Cary Grant, then you’ve probably never seen His Girl Friday. One of the absolute classic screwball comedies of Hollywood’s Golden Age, it was a definitive role for Grant as a hard-boiled newspaper editor. It’s actually fairly progressive, or at least tries to be, as beautiful star Rosalind Russell plays her reporter role vivaciously and plans to leave the scheming Grant behind her before getting caught up in the news story of the decade. The pair have a comic chemistry that has rarely been seen in the near-75 years since, and the movie moves so fast that you hardly have time to breathe. Every joke ever made about fast-talking 1940s newspapermen had its source in this movie.


8. Monsoon Wedding (2001)
It would be a crime to leave foreign romances off this list entirely. The Indian Monsoon Wedding is a little hard to describe, but suffice to say it plays out a little bit like Father of the Bride meets My Big Fat Greek Wedding, except, you know … Indian. The film centers on a father and daughter organizing a huge arranged marriage and family reunion, which offers an interesting inversion of a few typical Hollywood romantic comedy formulas as well as a broad satire on Indian society. It’s consistently funny and was a big domestic hit in India, with a musical adaptation poised to premiere on Broadway this year.


9. The Brothers Bloom (2008)
If The Brothers Bloom came out in 2014, we’d probably be looking at Wes Anderson-like success for the film, but way back in 2008, a lot fewer people were familiar with director Rian Johnson. Sure, there were devoted fans of his neo-noir Brick, but it wasn’t until the runaway success of 2012’s Looper that he was put on the map as an ascendant Hollywood director. This earlier tale of con men brothers was a great star vehicle for Adrian Brody and Mark Ruffalo in particular, whose performance then hinted at the comic potential he would later display as Bruce Banner in The Avengers. Rachel Weisz is especially good as the bizarre love interest who gets brought along on a continent-spanning adventure. The complicated plot is a little wonky, but the romance is sweetly endearing and Johnson gives it a fun, globe-trotting panache.


10. Casablanca (1942)
Casablanca is famous as a romance, but it’s really so many things at once. You’ve got the elements of a war film, a noir and a pulpy crime film all swirling around one of screendom’s best cases of natural chemistry between Humphrey Bogart and Ingrid Bergman. If you’ve never actually watched it, you may feel you already know everything there is to know about Casablanca, but it’s so much more than its quotable dialog and “As Time Goes By.” It grabs you and pulls you in immediately—nothing short of great popular entertainment.


11. Stranger than Fiction (2006)
Like Jim Carrey in The Truman Show, Will Ferrell deserved far more popular acclaim for his dramatic turn in Stranger than Fiction. Its excellent magical realism premise would have been enough to make for a promising film, but what Ferrell does here is wondrous—he crafts a character who is uniquely humble, reserved and average. Roger Ebert described the film as being about “quiet, sweet, worthy people,” and that is quite accurate. It’s a film that has an unexpected reserve of dignity, and its central romance between Ferrell and Maggie Gyllenhaal is seemingly mismatched but all the more genuine for it. Their first kiss is one of my favorite romantic film moments—totally vulnerable and adorable.


12. Fever Pitch (2005)
Now, as he assumes the mantle of The Tonight Show, it may be a good time to finally give Jimmy Fallon his due—although his film career has more than its fair share of bad movies (Taxi, anyone?), he put together an oddly endearing performance in this underrated, underseen flick. The premise makes you think it will simply be about Fallon’s character learning that “love is more important” than his die-hard Boston Red Sox obsession, but it ends up having a slightly deeper perspective on issues of vulnerability and abandonment. Fallon is undeniably charming, both funny and sympathetic. Drew Barrymore on the other hand is rather ditzy as the female lead, but compared to some of these other films Fever Pitch is fun, popcorn entertainment. And it’s a great way to get a sports fan to watch a romantic comedy.


13. Safety Not Guaranteed (2012)
Alright, we’re definitely on the fringes of “romance” now, but there’s still a sweet love story at the center of this down-to-earth comedy with a sci-fi premise. The relationship between Aubrey Plaza and Mark Duplass builds in unconventional and unexpected ways, and the audience is held in suspense throughout because they aren’t sure if either character’s stated feelings are a ruse. The nature of their emotions is very much dependent upon the unknown mental state of Duplass—is he crazy for thinking he can travel through time or simply an eccentric dreamer? The conclusion strikes exactly the right balance between possible payoffs.


14. Singin’ in the Rain (1952)
If Singin’ in the Rain isn’t the greatest of the classic American film musicals, then it’s at least so close as to make no difference. Sweet, earnest and genial, I personally find it a lot more entertaining than the likes of other romances such as West Side Story or Camelot. The characters are fun, and the music is incredibly infectious. If you’ve never seen it, there’s no way you’ll avoid finding yourself singing “Make ’Em Laugh,” “Moses Supposes,” “Good Morning” or the title track in the days that follow. The movie is like a well-worn pair of jeans that fits perfectly.