Narrowing down the greatest love stories, of any era, may very well be a fool’s errand. After all, practically every movie has a romantic subplot of one kind or another. It doesn’t matter if it’s a horror movie, an action movie, a biopic or a conventional rom-com; it seems like Hollywood doesn’t even know how to tell a story that doesn’t have a little love in it. That means there’s a lot of competition for the best romantic movies of the 21st century. Whittling the list down to 35 was an agonizing process, like assembling a puzzle that came with way too many pieces. No matter how we assembled it something noteworthy got left out.
So before we get started, let’s offer up our sincerest apologies to the celebrated Gosling Triad;The Notebook,Crazy Stupid Love,andLa La Landjust barely missed the cut. The same goes for feel-good Disney flicks likeEnchantedandWALL-E, superhero blockbusters likeWonder WomanandSpider-Man 2, and Oscar-winners likeThe Shape of WaterandCODA. But what remains is a rich assortment of romances from a variety of perspectives. Each one of these films will make you swoon, laugh, or cry, and probably a combination of all three. If hard-pressed, yes, these are the best romance movies of the 21st century (so far).
35’To All the Boys I’ve Loved Before' (2018)
Directed by Susan Johnson
We couldn’t have a list of romance movies and ignore the teen subgenre. High-school-set romances can feel a bit repetitive and contrived after a while. Jock meets geeky girl, popular girl falls for the nerdy loser – we’ve seen it all before. However, Netflix’s (and based on a novel byJenny Han)To All the Boys I’ve Loved Before, puts a different spin on the tired genre, focusing on the protagonist, and her relationship with her family as well as a love interest. Lara Jean Covey (Lana Condor), to conceal her crushes throughout the years, unleashes her emotions into a letter addressed to each crush. This is mainly to conceal her feelings towards Josh (Israel Broussard), her former best friend who is now dating her older sister, Margot (Janel Parrish).
When her younger sister sends out the letters, Lara Jean pretends to date another letter recipient, Peter (Noah Centineo). Lara hopes to throw Josh off and Peter wants to make his ex, Gen (Emilija Baranac), jealous. Yes,pretend-dating is a fairly overused trope in film, but there’s something fresh about howTo All the Boysapproaches it.Johnson’s film is as much about romantic love as it is about sisterly bonding and coming to terms with what love is really about.The two sequels are both fun but don’t match up to the sweet original. –Emma Kiely
To All the Boys I’ve Loved Before
34’Only You' (2018)
Directed by Harry Wootliff
A film that works to draw out the more realistic and somber truths of relationships,Only Youfollows Elena (Laia Costa) and Jake (Josh O’Connor) who meet one night while fighting over a taxi. As they fall in love, it seems that their relationship presents more challenges each day. Their 9-year age gap is something they can get past, but when they start trying for a baby, the journey of IVF, medication, and disappointment seems too overwhelming. The couple must then face the choice between each other and the life that they’ve always dreamed of.
It’s a rare thing when a film decides to look at what happens after the couple finally gets together. We don’t always get to watch as two people try to get through the day-to-day as a couple.O’Connor and Costa get right to the core of the film, making every scene rife with intimacy.It’s one of the morehonest portrayals of love and relationships in movies, but still grants the viewer a happy ending – one that you can actually see happening in real life.
Watch on Tubi
33’Love, Simon' (2018)
Directed by Greg Berlanti
The problem with a lot of teen romances is that the heroes are, obviously, teenagers. They are young and they are inexperienced, and it’s sometimes difficult to root for their love stories to have picture-perfect endings because we know their lives will be long, and filled with heartaches and romances for decades to come.Greg Berlanti’sLove, Simondeftly evades these notions, because it’s a coming-of-age story first and foremost, and what counts is how the protagonist grows upon having his first love, not whether or not they end up together forever.
Nick Robinsonstars as Simon, a gay teen who hasn’t come out yet, who forms a pen pal relationship with a mysterious fellow student, who also hasn’t revealed to his friends and family that he’s gay. The story forces Nick to make some tough choices, and he doesn’t always make the right one, but his journey to self-discovery gets his priorities in check, so he can come to terms with who he is and finally, possibly, have the romance he wants with someone he’s never met… except in his heart. And in his emails.A delightfully John Hughes-ian teen film with a sparkling ensemble cast.
Love, Simon
32’Once' (2007)
Directed by John Carney
John Carneyis famous the world over for making passionate, character-driven films full of awesome music, likeBegin AgainandSing Street. But his masterpiece is still this infectiously low-key, lovely romance.OncestarsGlen Hansardas a busker in Ireland, working in his father’s vacuum cleaner repair shop when he isn’t singing songs about his latest breakup in the street. When his music catches the ear of a Czech immigrant played byMarkéta Irglová, they strike up a friendship based on mutual, musical appreciation.
Naturally, they fall in love, but sadly, there’s nothing they can do about that. All they can do is scrape together whatever money they can, write some songs, and cut a record. Carney understands that the real thrill of watching their tale play out lies in watching the art his characters make, not in the contrived machinations of a story pushing them this way and that.There’s an intoxicating realness to thesimple yet heartfeltOnce, revelry in the power of music to connect with other human beings, that shines through and makes it truly special.
Watch on Hulu
31’Southside With You' (2016)
Directed by Richard Tanne
Richard Tanne’s intimate and absorbingSouthside With Youwould be one of thebest romantic movies of the decadeif its subjects were fictional. That it’s also based on the true story ofBarack ObamaandMichelle Robinson’s first date is but another intriguing selling point.Southside With Youfollows Robinson, played byTika Sumpter, as a young lawyer and Obama’s supervisor, who agrees to meet the summer associate for a community meeting. She hesitantly agrees to meet up earlier, but has no interest in an office romance.
Southside With Youtakes place over the course of the afternoon and early evening as these two individuals with powerful personalities share their thoughts on life, on politics, on race, and find a connection building between them. It’s not love at first sight, and it’s not a passionate love affair.Southsideis about two complex individuals with big ideas and serious dreams coming to realize, for the first time, that they could be more. Tanne’s film may not be able to fully escape a sense of mythologizing, and yet few romance movies in recent memory approach love and dating with the same confident maturity, regardless of the context.
Southside With You
Watch on Max
30’Deadpool' (2016)
Directed by Tim Miller
Quite a lot ofsuperhero movies have a love storyto tell amidst all the costumed crimefighting, but for some reason, it’s the one about a mass murderer who knows he’s in a movie that stands out.DeadpoolstarsRyan Reynoldsas a mercenary who finds the love of his life, Vanessa (Morena Baccarin), a hilarious, sensitive, intelligent, and sensual partner who makes his life worth living. So when he finds out he’s dying of cancer he flees to spare her the horror of watching him die, and he runs headlong into a secret government program that tortures him ruthlessly, in the hopes it will cure him and restore his life.
It is, of course, a devil’s bargain, and Deadpool emerges with superhuman healing powers but permanently marred skin, which only makes him more self-conscious about reuniting with his partner after so much of their relationship was physical. And at that point yes,there’s lots of action and violence and potty humor, butDeadpoolwould merely be a lark without a genuine, human story to ground it. And the story of a man whose insecurity nearly robs him of the relationship he wants, who ignores what his lover is telling him because he’s terrified that it’s not what she really needs, is far more thoughtful, accessible, and real than most of the other films in its genre.
29’Secretary' (2002)
Directed by Steven Shainberg
Not everybody loves each other the same way, and yet, few romantic movies seem genuinely interested in truly exploring a lifestyle of sexual kink. At least we haveSteven Shainberg’sSecretary.Maggie Gyllenhaalgives an electric performanceas a young woman who discovers, through an unexpected BDSM relationship with her new boss, that she’s a submissive who yearns for just the right dom.James Spaderplays her new lover, but even he doesn’t seem wholly comfortable with who he is and what he really wants.
Secretaryis an unusual film about people with very specific needs who find each other. Their desires may be specific, but their fantasy is universal: they’re looking for someone who loves them for who they are, who can provide what they need, and with whom they can be mutually happy. That’s a dream that should not merely be reserved for the sensually milquetoast. The kinky deserve true love too, andSecretaryis that rare love story that respects that everyone has unique needsand tells a lovely story that suggests there’s someone out there for everybody.
28'(500) Days of Summer' (2009)
Directed by Marc Webb
Easily one of the most influential and iconic romantic comedies of its era,(500) Days of Summerset the mold and status quo for many self-aware and convention-breakingrom-coms in the 2010s. The film follows the story of Tom (Joseph Gordon-Levitt), a hopeless romantic and greeting-card writer who has his life completely flipped upside down when his girlfriend, Summer (Zooey Deschanel), breaks up with him. The breakup causes him to reflect and reminisce on their 500-day-long relationship in order to figure out where things went wrong.
(500) Days of Summerenacts a unique style of self-deprecating humor and stylized execution that made it stand out greatly for its unique and hilarious approach to romantic comedy.It completely flips the genre of romantic comedy on its head in a way that few romcoms of the era were capable of. While certain aspects of its writing and characters haven’t particularly aged the best, it’s difficult to deny that the film had a massive influence on romantic comedies going forward.
(500) Days of Summer
Tom is a man who believes in true love. On the other hand, Summer is a more practical person who doesn’t want a serious long-term relationship. When their fates meet, the result is intense and complicated for him.
27’Lovers Rock' (2020)
Directed by Steve McQueen
The second film inSteve McQueen’sSmall Axecycle, a collection of films exploring the lives of West Indian immigrants in the 1960s, 1970s, and early 1980s, doesn’t so much tell a story as it seems to float, all on its own, throughout a brief and beautiful moment in time.Lovers Rocktakes place at a small house party where young people gather, absorb beautiful reggae music, and are swept away by their emotions… just like the audience.
To watchLovers Rockis to feel a rare kind of joy, the sensation that a movie has transported you to a specific place, and captured every single detail for you. The songs that fuel the soundtrack, the partygoers who know them all by heart, and a pair of young lovers who meet and share the exquisite glow of discovery amidst the jubilance and tumult that fueled their first moments. It’s ecstatic cinema, immersive and whole.
Buy on Criterion
26’Bridget Jones’s Diary' (2001)
Directed by Sharon Maguire
There were a couple ofgreat adaptations ofJane Austen’sPride and Prejudicein the early 2000s, but it’s this charming modern update that stands out the most.Bridget Jones’s DiarystarsRenée Zellwegeras Bridget, a woman caught in a love triangle between the dashing Daniel, played byHugh Grant, and the seemingly disinterested Mr. Darcy, played byColin Firth(who, in a bit of stunt casting, famously played Mr. Darcy in a straightforwardPride and Prejudiceadaptation six years prior).
It’s Zellweger’s film – she earned an Academy Award nomination for her performance – but directorSharon Maguirehas wonderfully furnished it for her.Bridget Jones’s Diarybrings all the smoldering romance and biting commentary of Austen’s novel into the modern-day, finding the tale just as relevant as ever and contemporary romantic expectations just as ripe for cunning commentary as those of the 19th century.
