Is there anything more delightful and life-affirming than a perfectly executed romantic comedy?
Every once in awhile, it’s nice to indulge our inner sap and just let our cynical expectations disappear as we sit back, grab a bucket of popcorn, pull up our Snuggie and pop in a cheesy feel-good (and completely unrealistic) rom-com. So here’s 20 romantic comedies we recommend for those days when you just feel like falling in love.
1) The Princess Bride (1987)
Westley: This is true love – you think this happens every day?
The quintessentially perfect book to screen adaptation, this film teaches us that even death cannot stop true love… it can only delay it for a while.
With its dashing pirates, deadly sword fights, and large animatronic rodents, The Princess Bride isn’t the traditional “kissing-book” romantic comedy. Its ironic humor makes it about so much more than the central romance, simultaneously mocking and yet believing in the power of this ultimate true love between a former stable boy and would-be princess.
2) 10 Things I Hate About You (1999)
Patrick: Ooh, see that, there. Who needs affection when I have blind hatred?
It’s hard to really mess up material from the king of romantic comedies himself, but this modern day interpretation of Shakespeare’s 400 year-old rom-com The Taming of the Shrew, shows us that despite hundreds of years of technological advancement, human behavior and emotion hasn’t really changed all that much through the generations.
And while we do not condone the objectification of women through a misogynistic bet, it’s hard to stay mad at a guy who literally did a song and dance routine in an attempt to win a lady’s affections.
3) You’ve Got Mail (1998)
Joe Fox: Don’t you love New York in the fall? It makes me want to buy school supplies. I would send you a bouquet of newly sharpened pencils if I knew your name and address. On the other hand, this not knowing has its charms.
It’s a real Sophie’s Choice trying to pick between Nora Ephrom’s two classic rom-coms starring Meg Ryan and Tom Hanks, but in the end this sequel of sorts to Sleepless in Seattle wins out because we get to watch these two fall in love twice: first as cyber pen pals, and later as enemies turned best friends.
Meg Ryan looks absolutely adorable in all of her granny sweaters, and makes us believe in the beauty of daisies as we wish we could all look so precious with a head cold. And everyone in this film works in a bookshop, which is just cool.
4) Penelope (2006)
Penelope: Once the Queen is dead, the King is useless.
Max: What’s that about?
Penelope: I don’t know. Maybe he’s too depressed to fight. He really loved her, you know.
This romantic comedy features Peter Dinklage as a cynical detective, James McAvoy as a jaded gambler who’s lost his musical soul, and Reese Witherspoon as a sassy
biker moped chick. Most importantly, Christina Ricci is the pig-faced damsel in distress who learns to slay her own dragons.
This quirky Beauty and the Beast interpretation turns the classic story on its head as the characters inspire one another to find their own strength as individuals, and proves that the most important person we have to learn to love is our self. Also, how cute are those chess scenes?
5) Music and Lyrics (2007)
Alex: The best time I’ve had in the last fifteen years was sitting at that piano with you.
Sophie: That’s wonderfully sensitive… especially from a man who wears such tight pants.
Alex: It forces all the blood to my heart.
This vastly underappreciated romantic comedy is wonderful in its simple, yet effective execution. Hugh Grant does what he does best and exploits his rom-com leading man status as a fallen pop star of the 80’s, while Drew Barrymore is adorable as his kooky plant-lady turned songwriter.
The actors are truly delightful in their chemistry, and their line delivery is absolutely spot-on as they make corny lines seem downright funny. Also, this cheesy pop soundtrack is just super catchy.
6) Breakfast at Tiffany’s (1961)
Paul Varjak: You know what’s wrong with you, Miss Whoever-you-are? You’re chicken. You’ve got no guts. You’re afraid to stick out your chin and say, “Okay, life’s a fact, people do fall in love, people do belong to each other, because that’s the only chance anybody’s got for real happiness.”
You call yourself a free spirit, a “wild thing,” and you’re terrified somebody’s gonna stick you in a cage. Well baby, you’re already in that cage. You built it yourself.
One of the more serious films on this list, this untraditional romantic comedy follows two lost souls as they stumble upon their love for each other.
She’s flighty and confused, he’s bored and losing hope. But no matter how hard it is for these two crazy kids to get there, at the end of the day, this film lets us believe that in our own way, we are all worthy of being loved.
7) The Wedding Singer (1998)
Sammy: If you find somebody you can love, you can’t let that get away.
This movie taught us what a perfect church-kiss looks like and gave us the soundtrack to our wedding photo album DVD. Also, Billy Idol is in it, and he’s fabulous.
And as far as the ending’s grand romantic gesture goes: the singing is bad, the lyrics are cheesy, and it’s still the most romantic song to be featured in a rom-com.
8) The Proposal (2009)
Margaret Tate: What am I allergic to?
Andrew Paxton: Pine nuts, and the full spectrum of human emotion.
A modern romantic comedy where neither of the characters is dumbed-down for the sake of plot, Margaret and Andrew are simultaneously funny and frustrating as they go from faking a proposal to falling in love.
Also, their chemistry is on fire in this film. So yes, we do believe that within the span of a weekend he went from hating his boss to proposing to her.
9) Clueless (1995)
Cher: Excuse me, but I have donated many expensive Italian outfits to Lucy, and as soon I get my license, I fully intend to brake for animals, and I have contributed many hours to helping two lonely teachers find romance.
Josh: Which I’ll bet serves your interests more than theirs. You know, If I ever saw you do anything that wasn’t ninety percent selfish, I’d die of shock.
Cher: Oh, that’d be reason enough for me.
Based on a book by one of the OG rom-com queens herself, this 90’s adaptation of Jane Austen’s Emma features one of Austen’s feistiest and most controversial heroines, and like the original material it’s based on, Clueless doesn’t shy away from exposing its heroine’s faults.
Cher is an anomaly of contradictions: smart, but ditzy; selfish, but giving; bratty, but genuinely sweet. It’s these contradictions, like Austen’s own Emma, that make us love her, and help us understand how a respectable, nerdy undergrad like our hero, Josh, could fall for his complicated, but ultimately kind-hearted teenage step-sister. Incest aside, it’s really very sweet. Oh, the 90’s… As if.
10) When Harry Met Sally (1989)
Harry: I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.
Finally: A romantic comedy where friendship and respect are at the core of a relationship. How beautiful is that?
In many ways, When Harry Met Sally is the mother load of romantic comedies because it popularized many of the rom-com tropes we now take for granted: characters meet and hate each other, only to later begrudgingly become friends and eventually fall in love.
This classic rom-com is so beloved because it’s also so realistic. Love is hard, and messy, and confusing, and no, it doesn’t usually all work itself out within the span of three days.
So, perhaps what’s most striking about this beloved film is that we know in our hearts that Harry and Sally are both far from perfect people, but in the end, we know that they are so perfect for each other.
11) She’s the Man (2006)
Duke: A few days ago I kissed this girl at a kissing booth, and now, I just can’t seem to stop thinking about her.
The list of great Amanda Bynes led romantic comedies is an extensive one. The girl definitely knew how to deliver a killer joke while giving her best flirty eyes, and her brand of charm and humor dominated the rom-com landscape for a while. We couldn’t make this list without including her!
The Amanda Bynes rom-com we’ve chosen to highlight is yet another modern play on Shakespeare. She’s the Man takes Twelfth Night and brings it to the boarding school soccer field, where Viola decides to impersonate her brother, Sebastian, in order to play the sport she loves.
Bonding over gouda and a lot of public flashing ensues as “Sebastian” grows closer to her roommate, Duke, and the result is a hilarious and heartfelt rom-com that deserves way more credit for launching Channing Tatum’s career.
12) Easy A (2010)
Olive: Whatever happened to chivalry? Does it only exist in 80’s movies? I want John Cusack holding a boombox outside my window. I wanna ride off on a lawnmower with Patrick Dempsey. I want Jake from Sixteen Candles waiting outside the church for me. I want Judd Nelson thrusting his fist into the air because he knows he got me. Just once I want my life to be like an 80’s movie, preferably one with a really awesome musical number for no apparent reason. But no, John Hughes did not direct my life.
Easy A definitely doesn’t start off as your typical rom-com. If anything, it reads as more anti-romance at some points. However, no matter how often Olive gets confirmation that everyone is terrible, she never actually loses faith in the possibility of love.
When Penn Badgley’s way-better-than-Dan-Humphrey woodchuck/lobster Todd comes back into the picture on a lawnmower, she’s reminded that some people live outside of the mob, and rumors don’t really matter as long as you, and maybe one other special person, know you’re a cool chick.
13) 13 Going on 30 (2004)
Jenna: I love you, Matt. You’re my best friend.
Because I still can’t hear the number 30 without thinking “flirty and thriving,” 13 Going on 30 gets the 13th spot on this list.
Jennifer Garner in 13 Going on 30 is a masterclass in charm that could only be matched by the endlessly adorable Mark Ruffalo. Their decades long, razzle fueled saga, set alongside Jenna’s transformation, is the perfect blend of cute and inspiring. This movie just makes you feel fantastic, and it’s largely because of the magic of the two leads.
14) Trainwreck (2015)
Amy: I like him so much. Why do I feel so scared.
Who said men get all the grand, romantic gestures? In Trainwreck, Amy is the commitment fearing mess that gets to come to her senses, in the end, winning the guy over and accepting the love she deserves.
Helmed by Amy Schumer and Bill Hader, it’s one of the funniest movies on this list, but that doesn’t take away any of its squee-worthiness. Also, if I’ve learned anything from High School Musical, it’s that you can never go wrong with a basketball-centric musical number.
15) To All the Boys I’ve Loved Before (2018)
Peter: There’s no one like you, Covey
Watching a great romcom is like sinking into a nice bath at the end of a long day — delightful, warm, and utterly relaxing. Which means watching To All The Boys I’ve Loved Before is like luxuriating in bath that’s the exact right temperature and filled with your bubbles from your best bath bomb from LUSH, all while holding a glass of your favorite wine.
To All The Boys I’ve Loved Before embraces the genre wholeheartedly, taking on tired tropes with a new energy and diverse casting choices. The film is sentimental without being cloying, sweet without being saccharine, but not afraid to turn up the heat (physically and narratively) when it needs to. It’s the story of a girl who loves the idea of love, and the boy who convinces her that though the reality of it can be scary, it’s also worth it.
Lana Condor is so loving and so easy to love as Lara Jean, and Noah Centineo is never so charming as when he’s playing Peter Kavinsky opposite of her. The movie does such a fantastic job at making you fall in love with their love — to the point where even though you know they aren’t real, you’re still rooting for them to be that one couple from high school (and there is always one) that ends up making it.
16) Friends with Benefits (2016)
Dylan: Why do women think the only way to get men to do what they want is to manipulate them?
Jamie: History, personal experience, romantic comedies.
Friends with Benefits is one of those gifts from the casting gods that you never knew you needed until you got it. Mila Kunis and Justin Timberlake are two of the coolest humans to walk the earth, so of course we want to watch them fall in love over the course of 90 minutes. Why didn’t anyone ask before?
The chemistry between the two leads is a huge part of the reason why this movie is more memorable than No Strings Attached, coincidentally starring Mila Kunis’s husband, Ashton Kutcher, and Natalie Portman. Honestly, it’s essentially the same movie and they were released around the same time, but it just can’t compare.
Friends with Benefits manages to make every second of Dylan and Jamie’s slow-burn romance adorable. From playing video games in their underwear, to working their way through oral sex, they somehow make our hearts melt the whole way through.
17) A Cinderella Story (2004)
Austin: I can be surrounded by a sea of people and still feel all alone… Then I think of you.
Just like Amanda Bynes, there were a couple years when it seemed like Hilary Duff was the go-to girl for rom-coms, and Chad Michael Murray was to go-to guy. In A Cinderella Story they came together to create a perfect piece of rom-com history.
Despite one of the most romantic scenes in A Cinderella Story taking place at a masquerade, the movie centers around both characters striving to be who they truly are. Sam refuses to compromise who she is to get the guy, and in the end, Austin throws away his father’s dream of football stardom to embrace his poetic side and to get the girl.
In the end, they rode off into the sunset toward an uncertain future, but not before they took a stand for themselves and kissed in the rain after a drought.
18) The Big Sick (2017)
Emily: I didn’t heckle you, just woo-hoo’d you. It’s supportive.
This movie falls even more into the “make you believe in love” category, because it’s actually based on a true story! The Big Sick tells the beautiful, heartwrenching, wonderfully romantic tale of Kumail Nanjiani and Emily Gordon’s real life romance, which was briefly interrupted by a mysterious illness.
The connection between Kumail and Emily is palpable, and feels epic in a very modern and real way. You can’t help but root for the two of them to figure things out, no matter the odds.
19) The Holiday (2006)
Iris: I have found almost everything ever written about love to be true.
This is the only holiday movie on this list, but it’s more than deserving of the honor. The Holiday is comprised of not one, but two iconic rom-coms, all wrapped up into one, amazing, holiday package.
Iris and Amanda are two women whose conviction to give up on love provokes them to spend the Christmas season in another part of the world. As luck would have it, even though they may not see it that way immediately, love is there waiting for them.
All four characters in The Holiday have been ripped apart by love in one way or another, before the movie finally brings them to the person who makes it all worth it. It will definitely be a part of our Christmas movie traditions for years to come!
20) Notting Hill (1999)
Anna: I’m also just a girl, standing in front of a boy, asking him to love her.
Two of the OG rom-com elites make true magic happen in Notting Hill. Hugh Grant and Julia Roberts are at their best in this movie, bringing William and Anna to life in a way that nobody else could.
Notting Hill is a classic case of something that shouldn’t work actually being the most perfect thing to ever exist. When the two lovers from opposite sides of the tracks come together, they make rom-com history.
What’s your favorite rom-com to rewatch?
Last updated September 2019. Additional reporting by Kendra Cleary and Lelanie Seyffer.
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