25 Romantic Comedies Every Woman Must See
There was a time when I was one of those contrarian "I'm not really a romantic comedy kind of girl" girls. I was raised on a steady diet of action movies, courtesy of my dad, who tends to be of the opinion that movies only get better with each massive onscreen explosion. When I was 2 years old and rode The Great Movie Ride at Disney, legend has it that I thought the alien from Alien (which has a mild scare moment in the ride) was one of the park characters and held out my autograph book for him to sign. That was the level of my desensitization.
Then, in high school, I watched When Harry Met Sally for the first time, and I was hooked. In truth, I had never really hated romantic comedies, as I would have had people believe. I saw them with my friends and really enjoyed anything with a female lead who worked at an approximation of Cosmopolitan or Vogue (I'm looking at you, How to Lose a Guy in 10 Days and 13 Going on 30). But when your all-time favorite movie becomes When Harry Met Sally, you can only keep up the "I don't really like RomComs" schtick up for so long.
I've come to accept (nay, embrace) the RomCom's place in cinematic history. Here are 25 romantic comedies that every woman should at least give a chance.
When Harry Met Sally
The modern classic. The new gold standard of romantic comedies. When Harry Met Sally has reigned supreme in the RomCom world since 1989, but it's more than just a romantic comedy; it's a hysterical comedy about men, women and friendship. And it's so much more than the "I'll have what she's having" scene.
Woody Allen's most famous film, Annie Hall is the story of two neurotic people trying to find love in this crazy world. It's infinitely quotable and definitely worth a viewing, if only to be part of the cultural conversation.
Isn't it just the worst when your boss starts dating the coworker you've had your eye on? And isn't it even worse when they do the deed in your apartment, which you've taken to letting people borrow as a sex den? This was in 1960, making it quite the progressive movie.
The Shop Around the Corner
If you've seen You've Got Mail, get ready for some deja vu with The Shop Around the Corner. Shop came first, but the story (about two people who can't get along in real life, but fall hard for one another via anonymous correspondence) proved timeless when Nora Ephron updated the tale for the email age.
Bringing Up Baby
Katherine Hepburn and Cary Grant set the bar for the screwball comedy in Bringing Up Baby. It's hilarious and essential viewing for your friendly debates about Manic Pixie Dream Girls and strong women in cinema.
Breakfast at Tiffany's
You need to see Breakfast at Tiffany's to finally validate that Audrey Hepburn poster you hung on your wall all through college. Also, Audrey is a goddess and in full Audrey form here.
The Princess Bride
Passing on seeing The Princess Bride? Inconceivable! (Sorry, I couldn't resist.) Seriously though, the cult classic is a timeless love story with enough humor and action to keep even the most restless romantics' attention.
Anyone who has ever felt ignored or neglected can enjoy a little catharsis watching Sixteen Candles, in which Molly Ringwald's family actually manages to forget her Sweet 16. It's also the kind of movie that gives hope to the nerdy sophomore in all of us, proving that, against all odds, anyone can get their Jake Ryan.
Pretty In Pink
Pretty In Pink might just be the defining high school love story. It's your classic Romeo & Juliet story: A girl from the wrong side of the tracks (she shops at thrift stores!) falls for the Poor Little Rich Boy. There's unrequited love (DUCKY!!) and Molly Ringwald in her teen queen prime.
The image of John Cusack holding up that boom box is one of the universal symbols of romance in American pop culture. Even if you've never seen Say Anything, you know exactly which scene I'm talking about. You have to see the movie that made that a thing. You just have to.
(500) Days of Summer
Sure, (500) Days of Summer might seem like an anti-romantic comedy in some ways, but it touches on some of the most honest and painful aspects of love — those times when it's one-sided or clouded by desperate optimism. Plus, even as the not-so-perfectly-matched Summer and Tom, Zooey Deschanel and Joseph Gordon-Levitt kill it with their onscreen chemistry.
Surprised to see Groundhog Day on a list of romantic comedies? Bill Murray relives the same day for years on end until he successfully woos Andie MacDowell. If that's not romance, what is?
Something's Gotta Give
Diane Keaton as a playwright. Jack Nicholson as a womanizer who notoriously chases younger women (so basically, as himself). A beach house. A heart attack. This is sounding well less romantic and way less sexy than it actually is. You have to see this one to get it, but it's so worth the investment.
The 40-Year-Old Virgin
Speaking of older protagonists getting it on, let's not forget The 40-Year-Old Virgin. This is a movie that will remind you that no matter how awkward you feel on the dating scene, it can always get worse.
Bridget Jones' Diary
When you think about watching a romantic comedy with your best girlfriends and a stick of cookie dough a piece, Bridget Jones' Diary is the RomCom you're thinking about watching. It's funny, filled with lady-friendly humor and sharp wit. The protagonist proves that beauty does exist beyond a size two, and the love triangle puts Twilight to shame.
This is one of those movies that you'll have a hard time avoiding. We all have a friend whose favorite movie of all time is Love Actually, and she's always trying to get everyone to watch it at every opportunity. Give in, get it over with and join the discussion.
While You Were Sleeping
When it comes to wacky RomCom setups, While You Were Sleeping is up there. Sandra Bullock pulls off a character who, in the wrong hands, would be like Morello in season two of Orange Is The New Black. Of course, when Sandy plays her, she's adorable.
Sleepless in Seattle
If there's one pairing that's most renowned in the modern RomCom world, it's Tom Hanks and Meg Ryan. See Sleepless in Seattle for their most famous onscreen coupling.
It's your classic hooker-meets-rich-guy love story. OK, it's the only classic hooker-meets-rich-guy love story. Still, you can't miss the movie that made Julia Roberts America's Sweetheart (for, remember, playing a hooker — that's impressive).
My Best Friend's Wedding
Please don't take a page from Julia's book in this one. She's kind of terrible (even though if you've ever had one that got away, you'll probably relate), but the movie is a must-see.
10 Things I Hate About You
Who would have thought that Shakespeare would work so perfectly set in a '90s high school? But it does work, and 10 Things I Hate About You features one of the most romantic scenes in the teen RomCom genre: Heath Ledger singing on the bleachers. Swoon.
Another classic lit update, Clueless is a cross-genre classic. No woman should make it through life without being able to quote at least three lines from this movie.
13 Going on 30
This brings us to the Lady Mag Journalists section of the list. In 13 Going on 30, Jennifer Garner plays a 13-year-old trapped in a 30-year-old's body thanks to a bizarre wish to skip to being "30, flirty and thriving" (I don't think I ever wanted to be 30, even as a child with no sense of time). Still, it's Big for girls with a little Mark Ruffalo love interest thrown in for good measure and it'll remind you to view the world through a child's eyes every now and then.
The Devil Wears Prada
There's not a lot of romance in this comedy, based on author Lauren Weisberger's real life experiences working at Vogue magazine. Still, it's refreshing to see the protagonist of a Lady Mag Journalist movie truly put her career first and not end up screwed over by it in the end. The real romance here is the long, hard courtship of Andy and Miranda. It's like a professional RomCom. Take notes.
How to Lose a Guy in 10 Days
How to Lose a Guy in 10 Days is kind of a modern screwball comedy and it's just the best. The plot is classic RomCom all the way, and Kate Hudson and Matthew McConaughey have ah-mazing chemistry.
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