The 12 Best Enemies-To-Lovers Movies Ever, Ranked

There's a reason that the "enemies to lovers" trope is such an enormous part of pop culture. On the small screen, you've got couples like Chuck Bass and Blair Waldorf (Ed Westwick and Leighton Meester) on "Gossip Girl," Buffy and Spike (Sarah Michelle Gellar and James Marsters) from "Buffy the Vampire Slayer," and, of course, Sam Malone and Diane Chambers (Ted Danson and Shelley Long) on "Cheers." So what about this trope on the big screen?

Plenty of movies feature an enemies to lovers arc, but which ones are the very best? For the purpose of this ranking, we should note that, to be honest, all of these movies execute this trope pretty much perfectly, so it's not so much a ranking from "worst to best" as it is "pretty good to flat-out excellent." With that in mind, here are twelve completely excellent, delightful, and engrossing enemies to lovers movies ... ranked. (Also, as a nice little bonus, a whole bunch of them have runtimes well under two hours, so binge a bunch of these right in a row if you feel so inclined!)

The enemies to lovers trope often goes hand in hand with the "fake couple" trope — which, obviously, means that two people need to pretend to be in a relationship for some plot-related reason — and that's precisely what happens in the 2009 romantic comedy "The Proposal." When publishing executive Margaret Tate (Sandra Bullock) realizes that she might get deported from New York back to Canada over a visa issue, she talks her beleaguered assistant Andrew Paxton (Ryan Reynolds) into marrying her so she can get a green card, promising him a promotion in the process.

As a part of their ruse, Andrew brings Margaret home to the small town of Sitka, Alaska to meet his family, including his stern father Joe (Craig T. Nelson) and doting mother and grandmother Grace and Annie (Mary Steenburgen and Betty White). Clearly, Margaret and Andrew do start developing real feelings for each other during their time in Alaska ... particularly as Andrew sees the softer, kinder side of his often domineering boss. Reynolds and Bullock have phenomenal chemistry, and thanks to a particularly funny turn from the late, great White, this movie definitely belongs in the enemies to lovers hall of fame.

Cast: Ryan Reynolds, Sandra Bullock, Betty White
Director: Anne Fletcher
Rating: PG-13
Runtime: 108 minutes
Where to watch: Buy or rent

Speaking of beleaguered assistants, when we meet both Harper Moore and Charlie Young in 2018's "Set It Up" — played by Zoey Deutch and Glen Powell, respectively — they're struggling to please their demanding bosses, sports journalism maven Kirsten Stevens (Lucy Liu) and venture capitalist Rick Otis (Taye Diggs). After a chance meeting picking up dinner orders, Harper and Charlie, who don't like each other very much at all, concoct an idea: what if their bosses simply dated each other? Would they maybe relax a little bit at work?

Kirsten and Rick actually hit it off pretty quickly, easing both Harper and Charlie's workload ... but the two end up intervening when both Rick and Kirsten neglect the relationship in favor of their jobs. Along the way, Charlie and Harper bond over their own personal ambitions — Charlie wants to work in a higher position at Rick's firm, while Harper dreams of being a sports journalist instead of toiling as Kirsten's assistant — and after Charlie's girlfriend grows distant over his demanding job, sparks fly between him and Harper. "Set It Up" is an absolute delight, one of Netflix's very best original rom-coms, and absolute proof that both Deutch and Powell are phenomenal performers.

Cast: Glen Powell, Zoey Deutch, Taye Diggs, Lucy Liu
Director: Claire Scanlon
Rating: R
Runtime: 105 minutes
Where to watch: Netflix

Based on William Shakespeare's comedy "The Taming of the Shrew," Gil Junger's 1999 teen comedy "10 Things I Hate About You" finds its titular "shrew" in Kat Stratford, a prickly, acerbic senior at Padua High School played by Julia Stiles. When Kat's popular younger sister Bianca (Larisa Oleynik) tells their overprotective dad Walter Stratford (a beautifully cast Larry Miller) that she wants to go on a date, he devises a rule: Bianca can date when Kat does. Because Kat is so firmly against the idea, Bianca's would-be suitor Joey Donner (Andrew Keegan) pays another student, the mysterious and Australian Patrick Verona (Heath Ledger), to woo a frankly unwilling Kat so that he can ask Bianca out; meanwhile, Bianca is quietly developing a crush on new student Cameron James (Joseph Gordon-Levitt), who's already head over heels in love with her.

Between Stiles and Ledger's phenomenal onscreen connection and a crackling, hilarious script by Karen McCullah and Kirsten Smith (who can forget bon mots like "that must be Nigel with the Brie?!"), "10 Things I Hate About You" isn't just a great teen movie, but an excellent take on an age-old enemies-to-lovers story updated for our modern times.

Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
Director: Gil Junger
Rating: PG-13
Runtime: 97 minutes
Where to watch: Disney+

To say that Patrick Swayze's Johnny Castle is deeply unimpressed by the young, impressionable, and naïve resortgoer Frances "Baby" Houseman (Jennifer Grey) when he first meets her in 1987's "Dirty Dancing" is a severe understatement. (Apparently, enmity between Swayze and Grey was a thing on the set of the film as well.) While Baby and her family spend their summer at a resort in the Catskills, Johnny works there as a dance teacher and entertainer — and when Johnny's dance partner Penny Johnson (Cynthia Rhodes) is unable to dance with him and he might lose out on a season's worth of salaries, Baby ends up training to be his new partner.

Not only is "Dirty Dancing" an affecting portrait of Baby's summer of self-discovery, it's also a wildly progressive film for its time (Penny can't perform after receiving a poorly performed abortion and only survives because Baby's father, who happens to be a doctor and is played by Jerry Orbach, steps in and saves her life). By the time Baby leaps into Johnny's arms for a spectacular life as "(I've Had) The Time of My Life" rings out, you'll be rooting for Baby and Johnny, an unlikely duo turned couple, to make it.

Cast: Patrick Swayze, Jennifer Grey, Jerry Orbach
Director: Emile Ardolino
Rating: PG-13
Runtime: 100 minutes
Where to watch: Buy or rent

The summer of 2020 was a bleak time for pretty much everybody, but at least we got a truly phenomenal enemies-to-lovers romantic comedy out of it. In July of that year, Max Barbakow's directorial debut "Palm Springs," produced by Andy Samberg and his loyal Lonely Island cohorts Akiva Schaffer and Jorma Taccone, hit Hulu after a bidding war at Sundance in January, giving Samberg and his co-star Cristin Milioti a chance to shine in a charming time-loop comedy.

When Sarah (Milioti) heads to a Palm Springs resort for her half-sister's wedding, she meets Nyles (Samberg), an affable but strange guy who seems to know her and convinces her to leave the reception to go hook up in the desert. Then, Sarah wakes up the next morning only to realize that the previous day, November 9, is repeating itself ... and as it turns out, Nyles has been stuck in this loop for quite some time. Though Sarah's in denial about her apparent fate at first, she realizes she has to open up and trust Nyles if they ever want to make it out of the loop. "Palm Springs" is funny, heartfelt, features winsome performances from Milioti, Samberg, and supporting player J.K. Simmons, and is absolutely worth checking out if you haven't seen it. (Also, the Lonely Island guys broke a longstanding Sundance sales record by 69 cents, which is just really great lore.)

Cast: Andy Samberg, Cristin Milioti, J.K. Simmons
Director: Max Barbakow
Rating: R
Runtime: 90 minutes
Where to watch: Hulu

What if a fictional First Son of the United States and a prince of England fell in love?! That's the question posed by 2023's "Red, White & Royal Blue," based on Casey McQuiston's bestselling queer romance novel of the same name. When the aforementioned First Son, Alex-Claremont Diaz (Taylor Zakhar-Perez), travels to London for a royal wedding, he ends up causing an international incident when he and Prince Henry (Nicholas Galitzine) start to tussle and end up bringing the massive wedding cake crashing to the ground. As a result, the two men go on a charm offensive, claiming that they're the best of friends ... and eventually, they start to fall in love.

From Alex's emotional self-discovery arc — in that he fully comes to terms with his bisexuality — and the sweet on-screen chemistry between Zakhar-Perez and Galitzine, "Red, White & Royal Blue" is a genuinely lovely romantic fantasy, even if Uma Thurman's thick accent as a Texan president is slightly distracting. There aren't enough great queer rom-coms in the world just yet, and it's great that this one provides some much-needed representation.

Cast: Taylor Zakhar-Perez, Nicholas Galitzine, Uma Thurman
Director: Matthew López
Rating: R
Runtime: 118 minutes
Where to watch: Amazon Prime Video

Robert Wise's landmark 1965 movie musical "The Sound of Music" might not immediately come to mind when you think of the enemies-to-lovers trope, but don't forget that when Captain Georg von Trapp (Christopher Plummer) first meets his brash new governess Maria (Julie Andrews), he's not exactly pleased by her off-the-cuff comments and sense of childlike wonder. Maria, who was recently ejected (more or less) from an Austrian convent because she constantly flouted the rules set by the other nuns, ends up bonding with the Captain's seven children, and eventually, he starts to see just how charming she is.

It's important to note that "The Sound of Music" begins with a whimsical, light-hearted story only to build to a third act where the Captain and Maria, who are now newlyweds, must escape Austria to evade Nazi forces — but it's still one of the best movie musicals ever made, and Andrews and Plummer both shine in their romantic roles. While it's a less conventional enemies to lovers movie, it definitely fits the bill.

Cast: Julie Andrews, Christopher Plummer
Director: Robert Wise
Rating: G
Runtime: 174 minutes
Where to watch: Disney+

"Singin' in the Rain" isn't just one of the best movie musicals ever made, if not the best in the entire genre — it's also a sneaky enemies-to-lovers movie! As movie stars Don Lockwood (Gene Kelly) and Lina Lamont (Jean Hagen) rule Hollywood in the era of silent films, the release of the (real movie) "The Jazz Singer" shakes up the entire industry and pivots it towards "talkies." As far as Don and Lina are concerned, there's one big problem: Lina can't sing, and her speaking voice is ... jarring (the voice that Hagen dons for Lina is, truly, one of the funniest things ever committed to film).

Enter Kathy Selden (Debbie Reynolds), an aspiring stage actress who can sing and ends up dubbing over Lina's voice in a new in-universe movie musical, "The Dancing Cavalier." Kathy and Don don't get along at first — she disparages film acting and he, quite obviously, takes umbrage — but as the movie unfolds, the two fall in love, leaving Don determined to make sure she gets credit for her outstanding work. "Singin' in the Rain" is still a delight decades after its 1952 release, and it's a great story of enemies turned lovers to boot.

Cast: Gene Kelly, Donald O'Connor, Debbie Reynolds, Jean Hagen
Director: Gene Kelly, Stanley Donen
Rating: G
Runtime: 103 minutes
Where to watch: HBO Max

Once you put all of the tiresome "ew, she kissed her stepbrother!" arguments about the 1995 movie "Clueless" aside, you'll realize it's a great enemies-to-lovers movie (and an adaptation of Jane Austen's "Emma" to boot). When we first meet Cher Horowitz, a ditzy but bright California teen played by Alicia Silverstone, she basically rules her Beverly Hills high school alongside her best friend Dionne Davenport (Stacey Dash), but not with an iron fist ... which is why she invites a new student, Tai Frasier (Brittany Murphy), into her little clique. Throughout the movie, we see Cher interact with her former "stepbrother" Josh, played by Paul Rudd — Cher's high-strung litigator father Mel (Dan Hedaya) only briefly dated Josh's mother, but still cares for the college student — but it isn't until Cher has a failed relationship with a high school peer named Christian Stovitz (Justin Walker) that she realizes the guy of her dreams has been there the whole time.

Again, the debate over Cher and Josh is frankly pretty dumb, and the truth is that they make a great couple; Cher helps Josh be less self-serious, and Josh encourages Cher to look beyond her own wants and needs and think about others. Amy Heckerling's update of "Emma" is hilarious, sweet, and heartfelt — and yes, Cher and Josh dating is completely fine.

Cast: Alicia Silverstone, Paul Rudd, Dan Hedaya
Director: Amy Heckerling
Rating: PG-13
Runtime: 97 minutes
Where to watch: Paramount+

Director Joe Wright is no stranger to luxurious, romantic period pieces — his filmography also includes "Atonement" and "Anna Karenina" — and there's no question that his 2005 adaptation of Jane Austen's "Pride & Prejudice" is considered one of the very best on-screen versions of this enemies-to-lovers story. The Bennet family is full of eligible bachelorettes, including Elizabeth (Keira Knightley), but she's largely uninterested in the idea of marriage; meeting the standoffish wealthy bachelor Mr. Darcy (Matthew Macfadyen) doesn't endear her to the prospect. As Darcy's nemesis George Wickham (Rupert Friend) romances Elizabeth's sister Jane (Rosamund Pike), the two end up spending more time together, and if you don't swoon when Darcy finally confesses his love to Elizabeth, you might be slightly dead inside (to say nothing of Darcy's Internet-famous hand flex).

Knightley and Macfadyen are electric on screen together — it's actually hard to believe that this Macfadyen is the same guy who would go on to play the weaselly Tom Wambsgans on "Succession" years later — and though this story is familiar, Wright's version makes it clear that it deserves to be told. Enemies-to-lovers arcs don't get much better than this.

Cast: Keira Knightley, Matthew Macfadyen, Rosamund Pike, Donald Sutherland
Director: Joe Wright
Rating: PG
Runtime: 127 minutes
Where to watch: Netflix

Funnily enough, Sharon Maguire's 2001 romantic comedy "Bridget Jones's Diary" and its source material, Helen Fielding's novel of the same name, are both modern versions of "Pride & Prejudice" — and in the film version, Renée Zellweger is absolutely perfect as the titular heroine. (She actually, believe it or not, earned an Oscar nod for her performance.) Bridget is incredibly relatable and quite a bit less prickly than Elizabeth Bennett — she simply wants to drink less, lose some weight, and meet the man of her dreams while working for a publishing company in London — but "f**kwits" like her boss, Daniel Cleaver (Hugh Grant, at his most charming) tend to derail those goals. When Bridget meets Mark Darcy (Colin Firth) at her mother's annual "turkey curry buffet" on New Year's Day, neither one of them is charmed, but as Bridget carries on with Daniel, Mark steps in to warn her about the guy ... and along the way, he tells Bridget he likes her just as she is, in one of the most sweetly romantic scenes in rom-com history.

Zellweger's Bridget has starred in three sequels to date, but the original is still the best, pitting Grant and Firth against one another as they vy for Bridget's affections. Few movies are more charming than "Bridget Jones's Diary," and it's one of the best enemies-to-lovers arcs ever (thanks in large part to its excellent source materials).

Cast: Renée Zellweger, Colin Firth, Hugh Grant
Director: Sharon Maguire
Rating: R
Runtime: 96 minutes
Where to watch: HBO Max

How could any other enemies to lovers movie possibly top this ranking? When Sally Albright (Meg Ryan) and Harry Burns (Billy Crystal) first meet as they drive from Chicago to New York after both graduating from college, they instantly butt heads, thanks largely to the fact that Harry declares men and women can never really be friends because romance gets in the way. As "When Harry Met Sally..." continues, the two keep crossing paths and, eventually, decide that they should be friends, but Harry is right — and when they end up in bed together, they almost part ways for good.

This 1989 romantic comedy — helmed by the ideal team of director Rob Reiner and screenwriter Nora Ephron — is one of the best in the entire genre, and Ryan and Crystal have rarely been better as two bickering New Yorkers looking for love with everyone but each other. (Also, it features one of Carrie Fisher's very best non-"Star Wars" performances.) If you haven't seen "When Harry Met Sally..." before, change that immediately; it'll earn its place as one of your favorites by the time the credits roll.

Cast: Meg Ryan, Billy Crystal, Carrie Fisher
Director: Rob Reiner
Rating: R
Runtime: 95 minutes
Where to watch: Buy or rent