There's a reason the opposites-attract trope is one of the most popular staples of the rom-com genre: We love to see love conquer anything, including two supposedly mismatched souls. Though our minds often immediately go to enemies-to-lovers when we think of opposites attracting, a host of other dynamics come into play within this trope. Sometimes it's a class issue, like in Pride & Prejudice, or starkly different personality types, like in Along Came Polly.
Whatever vibe and pairing type you're drawn to, a movie is available to fill the void.
- 132 VOTES
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The Plot: Sometimes it takes a while (and a couple of failed relationships) to see what's been in front of you the entire time. Harry (Billy Crystal) and Sally (Meg Ryan) don't exactly hit it off during a long road trip after they graduate from college. Their biggest argument hinges on whether or not men and women can be friends without elevating the relationship to romantic levels. They put this theory to the test when they meet again a decade later and try to keep things platonic while they nurture a close friendship. Spoiler alert: It doesn't work.
Why It's Worth Watching: When Harry Met Sally avoids the whirlwind passionate love affair concept and gives audiences a very grounded love story that demonstrates a realistic love based on truly knowing and understanding a person despite their different ways of thinking. Although you have to wonder whether some of the intense hyper-passionate rom-com relationships might fizzle out after the credits roll, Harry and Sally feel stable and based on a real foundation that will last. Viewers are often swept away by epic do-or-die movie relationships, but it's good for movies to remind us what real and long-lasting love looks like. Estelle Reiner's iconic “I'll have what she's having” line doesn't hurt, either.
- Actors: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby, Steven Ford
- Released: 1989
- Directed by: Rob Reiner
- 218 VOTES
The Plot: If you wrote a love poem and serenaded your crush with it in high school English class, you'd be roasted until (and probably on) graduation. But suspend your disbelief during 10 Things I Hate About You when Kat (Julia Stiles) and Bad Boy Patrick (Heath Ledger) fall for each other. Kat goes from being a cynical and abrasive book-smart teen to openly airing her vulnerability.
Why It's Worth Watching: The one-liners in this rom-com are beyond iconic. Not only does Kat's teacher call her out on the chip on her white upper-middle-class suburban shoulders, but Chastity asking if you can just be “whelmed” is peak ‘90s humor. And don’t forget the paintball make-out scene to “Semisonic.” As far as coming-of-age enemies-to-lovers movies go, this one still hits over two decades later.
- Actors: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz
- Released: 1999
- Directed by: Gil Junger
- 36 VOTES
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The Plot: The wealthy and powerful Christopher (Ralph Fiennes) falls for Marisa (Jennifer Lopez) at a five-star ritzy hotel during an event. The twist? She's a maid and single mom who works at the hotel and just wanted a night out. Naturally, Christopher romances her, and their differences don't stop the pair from falling in love.
Why It's Worth Watching: When two people from very different upbringings and wage brackets ditch convention and pursue a relationship anyway, it's almost like a modern retelling of Cinderella without the glass slipper and pumpkin carriage. It's refreshing to see a movie about a divorced Puerto Rican single mom wooing a guy high up in the political chain and tax bracket. Their relationship feels genuine and authentic, and it was a great movie to kick off more diverse pairings back in 2002.
- Actors: Jennifer Lopez, Ralph Fiennes, Natasha Richardson, Stanley Tucci, Bob Hoskins
- Released: 2002
- Directed by: Wayne Wang
More Maid in Manhattan
- #81 of 137 onThe 100+ Best Movies For Date Night
- #93 of 152 onThe Best Movies of 2002
- #64 of 473 onThe 470+ Best Chick Flicks Ever
- 428 VOTES
The Plot: Julia Roberts plays a sex worker (Vivian) who catches the eye of a rich guy, Edward (Richard Gere), when he hires her as an escort to stuffy work events. Though they come from very different worlds, the duo finds common ground. Edward isn't the best guy because he cemented his wealth by hurting others (even though it's legal). However, Vivian helps him grow as a person and shifts his worldview.
Why It's Worth Watching: The power dynamics here are a little suspect, and the film does have a “save me” message, but on some level, the steamy rom-com shifted the view of sex workers by making Vivian a dynamic and lovable character. This is a stark contrast from the usually offensive characterizations of women in the oldest profession. That's not to say the film is perfect, but it was groundbreaking for its time. Plus, Vivian's laugh is infectious, and you can't help but root for this pair.
- Actors: Richard Gere, Julia Roberts, Ralph Bellamy, Jason Alexander, Laura San Giacomo
- Released: 1990
- Directed by: Garry Marshall
More Pretty Woman- #24 of 50 onThe Biggest Movies Of The '90s, Ranked
- #45 of 278 on'Old' Movies Every Young Person Needs To Watch In Their Lifetime
- #71 of 149 onMovies That Should Never Be Remade
- 530 VOTES
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The Plot: Good Girl Sandy (Olivia Newton-John) and Bad Boy Danny (John Travolta) meet over summer vacation and develop a short-lived relationship where Danny can ditch some of the macho man behavior he puts on at school. When Sandy transfers to his school, she realizes Greaser Danny isn't the same person she knew on vacation. But he can't stop himself from pursuing a relationship while they try to work past their fundamental differences to meet in the middle. Despite Sandy's nerdy disposition, she finds herself in the Pink Ladies clique that's essentially the counterpart to the Greasers. Add in some iconic musical numbers and you've got yourself a movie.
Why It's Worth Watching: What could be better than summer lovin'? Grease is a classic for a reason. Even people who typically turn their noses up at musicals are often drawn to the film. The music is brilliantly written (and catchy as can be), and the musical really broke barriers for the ‘70s. It’s definitely a movie of its time in terms of the lack of representation and some outdated ideology, but it stands the test of time.
- Actors: John Travolta, Olivia Newton-John, Stockard Channing, Jeff Conaway, Didi Conn
- Released: 1978
- Directed by: Randal Kleiser
More Grease- Dig Deeper...The Best Songs in Grease, Ranked by Singability
- And Deeper...Which Character From 'Grease' Would You Be, According To Your Zodiac?
- #50 of 149 onMovies That Should Never Be Remade
- 618 VOTES
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The Plot: Before we had the ease of texting, couples were relegated to email and chat rooms. The horror. Meg Ryan (Kathleen) and Tom Hanks (Joe) are at it again in You've Got Mail. The pair loathe each other in reality, because Joe owns a massive book chain store while Kathleen can barely keep the lights on in her small bookshop. Unbeknownst to them, they've been chatting it up (and falling in love) online. The anonymity of the internet allows the pair to get to know each other without the bias of reality, and they have to marry each other's online personae with who they are in real life.
Why It's Worth Watching: Back in 1998, You've Got Mail was a fascinating foray into the possibilities of technology at the time. We're now all accustomed to shady online dating behavior like catfishing, but the internet isn't all bad. It was a unique way to unravel an enemies-to-lovers relationship and dive into the notion that getting to know someone online, where you can be vulnerable anonymously, can entirely change your perspective on the depth and intentions of someone you know IRL. It was even somewhat of a precursor to online dating.
- Actors: Tom Hanks, Meg Ryan, Parker Posey, Greg Kinnear, Jean Stapleton
- Released: 1998
- Directed by: Nora Ephron
More You've Got Mail- #22 of 35 onGreat Movies That Take Place In Autumn
- #25 of 137 onThe 100+ Best Movies For Date Night
- #430 of 769 onThe Most Rewatchable Movies
- 723 VOTES
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The Plot: This classic musical from the '60s centers on a professor’s experiment to turn a young woman with a Cockney accent into a believable woman of high society. Eliza (Audrey Hepburn) agrees to the bizarre proposition, hoping it will help her in the job market. At first, she and Professor Higgins (Rex Harrison) don't particularly get along, but grow closer. Things get a bit complicated, however, when someone else from high society has his eye on Eliza.
Why It's Worth Watching: Anything with Audrey Hepburn is automatically a win. There’s definitely a case that Higgins doesn't deserve Eliza and doesn't care about the toll his experiment takes on her, so that makes investing in the coupling a bit more difficult. Still, the music and performances are classic, and it's a piece of genre history.
- Actors: Audrey Hepburn, Rex Harrison, Stanley Holloway, Wilfrid Hyde-White, Gladys Cooper
- Released: 1964
- Directed by: George Cukor
More My Fair Lady - 817 VOTES
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The Plot: Melvin (Jack Nicholson) is a romance writer who couldn't have a worse track record in the love department. Sure, he knows how to swoon on the page, but not so much in real life. When he reluctantly pet-sits his neighbor's dog, his icy exterior softens a bit. And though most people can't stand to be around him, one waitress, Carol (Helen Hunt), can tolerate him - and he finally chills out enough to woo her.
Why It's Worth Watching: There's something extremely satisfactory about watching an emotionally stunted man let down his guard enough to stop being so miserable. The title of the movie comes from a post-therapy session when Melvin wonders if this is as good as it gets. Positive therapy arcs are few and far between - even when it's desperately needed - especially in 1997. It's encouraging to see someone genuinely work toward self-care and wading the waters of mental health. The one-liners are iconic, and Melvin and Carol's budding romance adds a level of vulnerability and closeness not always seen in rom-coms.
- Actors: Jack Nicholson, Helen Hunt, Greg Kinnear, Cuba Gooding, Skeet Ulrich
- Released: 1997
- Directed by: James L. Brooks
More As Good as It Gets- #47 of 50 onThe Biggest Movies Of The '90s, Ranked
- #199 of 640 onThe 600+ Funniest Movies Of All Time
- #115 of 379 onThe Best Movies Of The '90s, Ranked
- 927 VOTES
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The Plot: Ah, the whole “I bet you can’t make the high school loser prom queen” trope. When popular jock Zack's (Freddie Prinze Jr.) friends bet him that he can't make the artsy nerd Laney (Rachael Leigh Cook) popular enough to win prom queen, he immediately starts worming his way into her heart.
After a makeover (which basically consists of him removing her glasses and getting his sister to mildly cut her hair), his plan starts to work a little too much. But once they actually get to know each other, their differences become less relevant, and they defy the stereotypes and assumptions they had about each other.
Why It's Worth Watching: For starters, the epic make-out scene to “Kiss Me” by Sixpence None The Richer has become such a pop culture staple that people can reference the scene having never watched the movie (or even knowing where the moment comes from). The concept of needing to change someone to fall in love with them is less than ideal, but try to look past that in this 1999 movie with an endless slew of swoon-worthy beats. The rom-com even spawned the 2021 Netflix movie He's All That, which takes place in a different universe but has cameos from She's All That actors Cook and Matthew Lillard.
- Actors: Freddie Prinze, Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O'Keefe
- Released: 1999
- Directed by: Robert Iscove
More She's All That- #242 of 379 onThe Best Movies Of The '90s, Ranked
- #33 of 473 onThe 470+ Best Chick Flicks Ever
- #38 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- 1018 VOTES
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The Plot: Lloyd (John Cusack) is infatuated with a beautiful girl, Diane (Ione Skye), who's far more interested in focusing on school than boys. Eventually, however, his charm wins her over. His Romeo and Juliet-esque pseudo-balcony serenade doesn't hurt, either. Naturally, her father is not pleased with this match, which makes it difficult for the high schoolers to pursue their feelings for each other.
Why It's Worth Watching: Whether you've seen the film or not, pretty much everyone has witnessed pop culture re-creations of the boom-box “In Your Eyes” serenade. Not only is the movie relatable, but both teens and adults can appreciate this love story.
- Actors: John Cusack, Ione Skye, John Mahoney, Lili Taylor, Amy Brooks
- Released: 1989
- Directed by: Cameron Crowe
More Say Anything...- #119 of 399 onThe Best Movies Of The 1980s, Ranked
- #149 of 278 on'Old' Movies Every Young Person Needs To Watch In Their Lifetime
- #43 of 137 onThe 100+ Best Movies For Date Night
- 1110 VOTES
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The Plot: Elizabeth Bennet (Keira Knightley) lives with her family in the English countryside, and she's not thrilled with the expectation that she must quickly enter into a marriage. Enter Mr. Darcy (Matthew Macfadyen): the polar opposite of Elizabeth. Elizabeth is in a very different social class than Darcy, and he's not exactly a guy willing to waver on his elitism. However, Elizabeth wins him over and breaks through his carefully maintained shell to let her in.
Why It's Worth Watching: Countless screen iterations of this story based on Jane Austen's novel have been released over the years, but this 2005 film version stands out. Anything with Knightley is sure to be a hit, and Macfadyen delivers an equally captivating performance. Despite the OG story's 1796 release, Elizabeth is extremely outspoken, with notes of feminism that were nearly unheard of during this time. While 2005 audiences wouldn't bat an eye at a strong-willed female character, it's important to note its origin and the impact this character had on literature.
More Pride and Prejudice- #658 of 769 onThe Most Rewatchable Movies
- #218 of 375 onThe Best Movies Based On Books
- #40 of 473 onThe 470+ Best Chick Flicks Ever
- 1232 VOTES
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The Plot: Most writers live their adventures through the pages of their books, but Joan (Kathleen Turner), ends up embroiled in a wild ride that could very well be a novel in itself (a fate it does meet). When her sister gets kidnapped, she has to trek to the Colombian jungle to hand off a treasure map to the people who kidnapped her sister. Meanwhile, a mercenary, Jack (Michael Douglas), helps her along the way and she falls for the rough-and-tumble bad boy.
Why It's Worth Watching: A good action-adventure romance movie ups the ante from typical rom-com settings, which typically have rather mundane settings - between high school or the workplace. Romancing the Stone has Raiders of the Last Ark vibes, which is a plus. Between crocodiles and gangsters, it's an intense and action-packed romance.
- Actors: Michael Douglas, Kathleen Turner, Danny DeVito, Zack Norman, Alfonso Arau
- Released: 1984
- Directed by: Robert Zemeckis
More Romancing the Stone- #53 of 399 onThe Best Movies Of The 1980s, Ranked
- #127 of 278 on'Old' Movies Every Young Person Needs To Watch In Their Lifetime
- #113 of 640 onThe 600+ Funniest Movies Of All Time
- 137 VOTES
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The Plot: Strategically conning your aggressive bosses into meet-cute scenarios to coerce them into dating just brings people together. The animosity between Charlie (Glen Powell) and Harper (Zoey Deutch) is palpable when they're somehow super competitive despite being assistants to different bosses. But given how savage their respective employers are, it's not surprising they need to channel that frustration elsewhere. When Harper gets the brilliant idea to set their bosses up without their knowledge, they have to work together. Romance ensues - obviously.
Why It's Worth Watching: Deutch can make just about any character charming with an infectious smile and quirky disposition. The chemistry between these two is off the charts, and any New Yorker can relate to the trials and tribulations of bringing pizza up a fire escape. Now that rom-coms are a blockbuster rarity, streaming services like Netflix often fill that void with high-quality movies that feel like they could be on the big screen. Set It Up is a wholesome enemies-to-lovers movie that proves why the opposites-attract trope still works.
- Actors: Zoey Deutch, Glen Powell, Lucy Liu, Taye Diggs, Joan Smalls
- Released: 2018
- Directed by: Claire Scanlon
More Set It Up- #14 of 71 onGreat Quirky Movies for Grown-Ups
- #25 of 58 onThe Best Movies About Millennials (So Far)
- #6 of 45 on25+ Romantic Comedies To Watch On Netflix Right Now
- 147 VOTES
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The Plot: It's a tale as old as time: workplace feuds often turn into unlikely romances (at least in the movies). TV producer Abby (Katherine Heigl) is tired of being single despite her extensive efforts to find a guy worth settling down with. Meanwhile, she's busy butting heads with TV star Mike (Gerard Butler) during a segment on that very same subject of modern relationships. Though she has to break through his infuriating misogyny, the duo is unable to fight the rage-fueled chemistry.
Why It's Worth Watching: Though Mike's toxic ideology regarding women is hard to get past, the chemistry is palpable. It's always nice to see genuine growth in a couple, and Mike and Abby are able to work through their differences to find common ground. Abby is resistant to taking dating advice from someone like Mike, but it's not surprising that this level of intimacy would lead to something more.
- Actors: Katherine Heigl, Gerard Butler, Eric Winter, John Michael Higgins, Bree Turner
- Released: 2009
- Directed by: Robert Luketic
More The Ugly Truth- #197 of 473 onThe 470+ Best Chick Flicks Ever
- #33 of 65 onRomantic Movies Your Girlfriend Forces You To Watch
- #206 of 245 onThe Best Movies For Women
- 154 VOTES
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The Plot: There's nothing like a type A actuary scorned to kick off an unlikely romance. After Reuben (Ben Stiller) splits from his cheating fiancee, he reconnects with his former classmate Polly (Jennifer Aniston). Unlike Reuben, who never takes risks and always has a plan in place, Polly is a free spirit who teaches him to live life with less red tape. They might make an unlikely pair on paper, but their particular quirks help balance each other out.
Why It's Worth Watching: The ferret, of course. Along Came Polly is as quirky as its the lead actors' personalities and scenes (some really awkward bathroom moments here), but it's still charming. Most movies follow the same formula with a rotation of a few different character types. Along Came Polly breaks the mold and gives some of its weirder audience members some hope that they, too, can find someone as odd and lovably neurotic as they are.
- Actors: Ben Stiller, Jennifer Aniston, Philip Seymour Hoffman, Debra Messing, Hank Azaria
- Released: 2004
- Directed by: John Hamburg
More Along Came Polly- #84 of 99 onThe Best Movies Of 2004, Ranked
- #384 of 473 onThe 470+ Best Chick Flicks Ever
- #29 of 70 onThe Best Movies About Getting Dumped
- 164 VOTES
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The Plot: A morbid 20-year-old with a fascination for death meets an 80-year-old woman and they develop a disturbingly taboo relationship with very uncomfortable power dynamics. So, where is Harold (Bud Court) and Maude's (Ruth Gordon) meet-cute? At a funeral, obviously. Yikes.
Why It's Worth Watching: The film helped define the opposites-attract trope back in 1971. It was highly rated at the time, and even still, some people think it's one of the best romance movies out there. It's wildly uncomfortable to watch a vulnerable, barely-out-of-his-teens young man with clear mental health struggles enter a relationship with a woman in her '80s - especially because he looks like he’s 12. The glamorization of topics of suicide isn't ideal, either. That being said, to understand the trope's history, you might be inclined to watch Harold and Maude.
- Actors: Bud Cort, Ruth Gordon, Cyril Cusack, Vivian Pickles, Charles Tyner
- Released: 1971
- Directed by: Hal Ashby
More Harold and Maude- #365 of 640 onThe 600+ Funniest Movies Of All Time
- #239 of 712 onThe All-Time Greatest Comedy Films
- #726 of 769 onThe Most Rewatchable Movies
- 174 VOTES
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The Plot: If you ask Kirk (Jay Baruchel), he doesn't have much going on in his life - between a job he hates and feeling like he's standing still in life. However, he meets a gorgeous woman, Molly (Alice Eve), who falls for him. Where he's flailing in his career, she's successful. Jay firmly acknowledges that Molly is out of his league (his words). Yet he's determined to make it work.
Why It's Worth Watching: It's pretty wholesome to see a guy with little to no self-esteem build back his confidence when a love interest convinces him he's worth it. Molly breaks through his pessimism and the idea that he's hopeless (a notion spurned on by his family and his ex). Even better? She doesn't need him to have a makeover or completely change himself to be “worthy” of her. She just likes him for him, and it's a refreshing change of pace from a lot of movies in the genre.
- Actors: Jay Baruchel, Alice Eve, T.J. Miller, Mike Vogel, Nate Torrence
- Released: 2010
- Directed by: Jim Field Smith
