That type of rom-com feels harder to find. But when you do find one that speaks to you so completely, it burrows itself into your heart and stays there nestled amongst your favorite movies. So, ahead of Valentine’s Day, we’re looking back at some of the best romantic comedies ever. Whether you’re celebrating with a partner, your BFFs, or getting in some much-deserved me time, these movies will leave you swooning way more than any roses or chocolate hearts could.
Notting Hill (1999)
I am of the mind that we throw around the phrase “GOAT” a bit too often, but when it comes to rom-coms, Julia Roberts and Hugh Grant are inarguably two of the greatest of all time to ever grace the rom-com screen. So it’s not surprising that when the duo brought together their amazing hair genes for Notting Hill — the Richard Curtis-penned (another genre legend thanks to movies like Four Weddings and a Funeral, Bridget Jones’s Diary and Love Actually) film about a British bookseller (Grant) and world-famous American actress (Roberts) who meet by chance and fall in love — created a classic. The result is as charming, witty, and wistful as the actors have proven themselves to be. I’m just a girl, standing in front of Hollywood, asking all romantic comedies to be this good.
Where to watch: Netflix
Set It Up (2018)
When people lament the state of the contemporary romantic comedy, one of the main complaints is that the lead actors don’t have that electric, sort-of magical, can’t-look-away-from chemistry that defines all of the best rom-coms. Set It Up stars Zoey Deutch and Glen Powell do not have that problem. Playing two tortured NYC assistants who attempt to set up their high-strung bosses (Lucy Liu and Taye Diggs) in order to get them thinking about things that aren’t work, it’s clear that the pair are immediately vibing on the same just-quirky-enough wavelength that makes you root for them while also wishing you could capture that energy IRL. Deutch and Powell are so good together that they should be making more movies together à la Tom Hanks and Meg Ryan, or Emma Stone and Ryan Gosling — it’s what we deserve.
Where to watch: Netflix
Palm Springs (2020)
Anyone who watched Brooklyn Nine-Nine knows that Andy Samberg has what it takes to be a romantic lead, so it’s delightful to see him doing just that in a movie opposite the always winning Cristin Milioti. It could have been easy for Palm Springs — which follows a couple of wedding guests who somehow get stuck in a time loop together, forcing them to relive the same day over and over again — to stick to the classic Groundhog Day formula. Instead the conceit is elevated, thanks to updated material (it was an accident that this movie came out early on in the pandemic, but boy did that make it resonate even harder) and two stars who can effortlessly go from irreverent to goofy to swoon-worthy in the same scene.
Where to watch: Hulu
10 Things I Hate About You (1999)
10 Things I Hate About You — a modernized version of William Shakespeare’s The Taming of the Shrew — has everything you could want from a teen rom-com. The framing (younger sister Bianca can’t date until her older sister Kat does; the boy who has a crush on Bianca arranges a bet with the school’s resident bad boy Patrick to get Kat to fall in love with him) is absurd, but in a fun, movie-worthy way. The cast is stacked (hello, Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Gabrielle Union, and Allison Janney). The romantic lead is definitely someone your teenage self would spend hours journaling about (again, hello, Heath Ledger), while Kat is both someone you can relate to and want to be best friends with.
Where to watch: Disney+
Plus One (2019)
I consider Plus One to be the most underrated rom-com of the last five years, which also means I consider it my sacred duty to get as many people as possible to watch it. The film follows two tight-knit college friends, Alice (Maya Erskine) and Ben (Jack Quaid), as they decide to embark on wedding season together, not wanting to attend ceremony after ceremony alone as they’re both single. They eventually fall in love, obviously. It may sound simple, but that’s what makes this movie work — every element of the film is executed at the highest level, with funny, grounded, touching performances from the two leads. Plus One shows a whole new side to Jack Quaid (especially if you’re most familiar with him from the in-your-face violence of anti-superhero show The Boys), and, in a just world, it would have made Erskine a household name. This is my plea to the masses: Watch this movie.
Where to watch: Tubi
Crazy Rich Asians (2018)
It’s impossible to watch Crazy Rich Asians and not get swept up in the lavish world the film creates. Constance Wu and Henry Golding star as Rachel and Nick, a happy couple traveling from New York to attend a wedding in Singapore, where Rachel will meet Nick’s closest friends and family for the first time. That’s when she discovers that Nick is from an obscenely wealthy family, is one of the country’s most eligible bachelors, and that his mother (Michelle Yeoh) doesn’t exactly approve of their relationship. The movie is lush, vibrant, big-hearted, and so romantic — even when Nick is making bad decisions, like not disclosing pertinent information to his long-term girlfriend. But, through all the glitz and grand gestures, Wu’s magnetic performance pulls you toward Rachel’s side; you want her to stand up for herself, you want her to choose what’s best for her, even if it’s not the easy thing, which is what truly makes this movie unforgettable.
Where to watch: HBO Max
The Best Man (1999)
The Best Man, is in part, about the undeniable pull between college friends Harper (Taye Diggs) and Jordan (Nia Long), which is reignited when Harper, who’s now a successful author, reunites with the rest of his pals for a wedding — despite being in a relationship with Robyn (Sanaa Lathan). The will-they-won’t-they of the love triangle is irresistible (duh, we’re talking rom-coms, after all), but The Best Man is also just as much about the authentic, life-like friendships between Harper and the rest of his college circle (including stars like Morris Chestnut and Harold Perrineau), and it feels all the more special for it.
Where to watch: Prime Video
The Big Sick (2017)
Typically, I avoid any romance movies that involve a life-threatening illness of some kind, but I’ll always make an exception for the smart and moving The Big Sick. Written by IRL married couple Kumail Nanjiani and Emily V. Gordon, the movie is inspired by their actual love story. (Nanjiani also plays a fictionalized version of himself, while Zoe Kazan portrays the on-screen Emily.) That’s part of what makes this movie so great — the sense that Nanjiani and Gordon are the only two people on this planet who could have written this story. Every laugh is full and genuine, and so are the (good) tears you inevitably will cry.
Where to watch: Prime Video
To All the Boys I’ve Loved Before (2018)
Every movie should have a Lara Jean Covey and Peter Kavinsky — except I don’t know that we, as a society, are prepared for that much cuteness. But that’s what you can count on the main couple in wholesome teen rom-com To All the Boys I’ve Loved Before for every time. Adapted from Jenny Han’s novel of the same name, the movie follows Lara Jean (a star-making turn from Lana Condor), a teen whose secret love letters have been mailed out to all her former crushes, forcing her to “fake date” high school jock Peter (a.k.a. the role that turned Noah Centineo into the internet’s boyfriend) to avoid the fallout. To watch To All the Boys is what it feels like to have a teenaged crush: It leaves you giddy, sighing dreamily, with carefree butterflies fluttering around in your stomach.
Where to watch: Netflix
Crazy, Stupid, Love (2011)
At 40, Cal Weaver's (Steve Carell) American Dream life is turned on its head. He finds out his wife, Emily (Julianne Moore), has been cheating on him, and also wants a divorce. Single for the first time in ages, Cal learns to navigate modern dating with the help of his ridiculously smooth, ridiculously flirtatious friend, Jacob (Ryan Gosling), who has a romantic fixation of his own daughter – Hannah (Emma Stone). Crazy, Stupid, Love isn't just about one couple; rather, it's an exploration about the nature of dating, coming together, and relationship expiration dates in general.
Where to watch: HBO Max
What If (2014)
Daniel Radcliffe and Zoe Kazan star in this under-the-radar modernization of the classic When Harry Met Sally conceit: Can men and women truly be friends? Turns out, we're still trying to answer that question, but Radcliffe and Kazan (plus delightful supporting roles from not-yet-incredibly-famous Adam Driver and Mackenzie Davis) are so charming while they do it.
Where to watch: Prime Video
Roman Holiday (1953)
Being a princess isn't all fun and tiaras, as Princess Anne (Audrey Hepburn) can tell you. During a tour of the European capitals, she's confined to a rigid schedule and has no freedom. Anne is filled with the spirit of rebellion while in Rome, and runs away from her entourage for a night. Things don't go as planned, and she's saved from certain doom by an American journalist named Joe Bradley (Gregory Peck). When Joe finds out Anne's identity, he sees the opportunity for one helluva juicy story. Rome is the perfect backdrop for this royal-commoner romance (and war of wits).
Where to watch: Paramount+
When Harry Met Sally (1989)
The first time Harry (Billy Crystal) and Sally (Meg Ryan) meet is on a road trip from Chicago to New York. Harry is sure that men and women cannot, under any circumstances, be friends — sexual tension will always get in the way. Sally disagrees vehemently, as she does with Harry on most issues. So begins a 12-year-long friendship made up of conversations much like this one. The majority of When Harry Met Sally consists of two people being witty, funny, and kind to each other. Essentially, being their best selves. After watching the evolution of their long friendship, it makes sense why they'd decide to get together. We've seen every step of the way.
Where to watch: HBO Max
You've Got Mail (1998)
In real life, Kathleen Kelly (Meg Ryan) and Joe Fox (Tom Hanks) are mortal enemies. Kathleen owns a small, indie bookstore, and Joe is the scion of a Barnes & Noble-esque conglomerate threatening the life force of stores like Kathleen's (funny that years later, indie bookstores are thriving and Barnes & Noble isn't.) But Kathleen and Joe have a vibrant, vivid relationship over email. You've Got Mail shows the divide between our in-person relationships and the crackle and sizzle often found in email (and now texts).
My Big Fat Greek Wedding (2002)
Toula's (Nia Vardalos) family can't understand why she doesn't want to get married. She's 29, and has lived her whole life among her Greek-American relatives, who all seem to be fixated only on marriage and procreation. Toula had bigger dreams for herself than working as a waitress in the family diner, but can't seem to escape her family's expectations. Until the day she meets Ian Miller (John Corbett), a dreamy English teacher whose WASP-y family is nothing like hers. They fall in love – now it's a matter of convincing her family that he's the one for her, even though he's not Greek. My Big Fat Greek Wedding is a celebration of all different kinds of love, and has some of the most iconic one-liners in movie history.
Two Can Play That Game (2001)
Shante (Vivica A. Fox) is used to being in the driver's seat of her romantic relationships, but Keith (Morris Chestnut) isn't easy to control. To keep him in line, Shante is willing to do anything — even if that means sabotaging her love life with petty games. Hey, it's not the most mature thing to do, but who hasn't been there?
Bend It Like Beckham (2002)
"Rom-com" is too narrow a classification for this big-hearted movie about tradition, parental expectation, and of course, soccer. At 18, Jess Bhamra (Parminder Nagra) is of the age when her Indian parents want her to start thinking of marriage. But she's far more interested in trying out for the women's soccer league near her house, even though her parents have expressly forbidden her playing sports. Jess is recruited by the team's star, Jules Paxton (Keira Knightley), who becomes her best friend. Then, she meets the coach, Joe (Jonathan Rhys-Meyers), and any chance at being set up goes out the window.
Something New (2006)
Kenya (Sanaa Lathan) has everything — a stellar career as a lawyer, a beautiful home — except for a partner. She wants someone who will check all her boxes, and Brian Kelly (Simon Baker), the landscaper she's just fallen for, definitely doesn't do that. Mark Harper (Blair Underwood), the man her friends introduce her to, was more what she was expecting: a Black, handsome professional. Kenya will have to choose between what she thought she wanted, and what she wants.
As Good As It Gets (1997)
Melvin Udall (Jack Nicholson) is the kind of man who your friends, family, and loved ones would tell you not to date. He's a gruff, reclusive genius who shirks company in order to write his romance novels, of all ironies. As Good As It Gets tracks his great softening from asshole to less-of-an-asshole, thanks to the help of a puppy, a friend, and the waitress (Helen Hunt) who gives him a chance.
Coming to America (1998)
In his home country, dating is close to impossible for Prince Akeem (Eddie Murphy). Everyone knows he's royalty, and just wants him for his status. So Akeem and his best friend Semmi (Arsenio Hall) travel to America — Queens, New York, to be precise – in order to find a woman who will love Akeem for Akeem. He takes a job working at a fast food restaurant, and falls for the owner's daughter, Lisa McDowell (Shari Headley). Lisa's father isn't thrilled that she's dating a man who, according to his own account, is a goat herder back home. Little do they know, Akeem is super rich – a quality that, as the Fifty Shades trilogy displays so perfectly, trumps all in the world of rom-coms.
Moonstruck (1987)
Loretta (Cher) thinks she's cursed. Her first marriage ended in her husband's sudden death. She's finally willing to get married again, to a friendly, if a little boring, Italian man named Johnny (Danny Aiello) under the condition that they do things the right way. She sends him to Sicily to tell his mother they're engaged. While Johnny's away, Loretta has to tell his brother, Ronny (Nicolas Cage), that they're engaged. Ronny, who's still sore about the accident that left him without a hand, wants nothing to do with his brother — and everything to do with Loretta. Alongside Ronny and Loretta's plunge into some crazy kind of love, there are a few other romantic storylines involving Loretta's neighbors in Brooklyn Heights.
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