13 Movies Where Best Friends Fall In Love
True best friends are hard to find. However, these movie best friends who fall in love dare to push past their safe places in order to leave the friend zone for a chance at romance.
In many ways, it makes perfect sense for best friends to fall in love. After all, they already know what to expect from their would-be partner in nearly every situation. Of course, it’s a gamble to leave the comfort of the friend zone. If the relationship doesn’t work out, chances are the friendship is over as well. Yet the characters in these rom-coms about best friends are willing to go all in for a chance at love. In Hollywood, at least, a happily ever after is almost always guaranteed.
- 1225 VOTESPhoto: Columbia Pictures
When Harry (Billy Crystal) first meets Sally (Meg Ryan), they start out hating each other. They share a drive from Chicago to New York City, during which they disagree about nearly every topic they discuss. They meet again years later and begin the most unlikely of friendships. Harry and Sally share all the juicy intimate details about their lives, beginning to disprove Harry's original notion that men and women can't be friends.
However, a moment of weakness threatens their friendship. Harry and Sally sleep together, and for a time it seems like that will ruin everything, But once Harry loses his bestie, he finally realizes that Sally can be both his friend and lover. They share a kiss at midnight on New Year's Eve, after Harry declares that “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.”
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Thirteen-year-old Jenna (Christa B. Allen and Jennifer Garner) makes a wish to be a 30-year-old. When she wakes up as a rich, successful New York City editor with her dream job at a fashion magazine and a posh lifestyle, Jenna thinks she has it all.
Then, she runs into her former neighbor/best friend Matt (Sean Marquette and Mark Ruffalo), who informs her what a terrible person she has become. Despite that, the two begin their friendship again as adults.
Matt helps Jenna learn a difficult lesson about loyalty and kindness, and it seems like the two of them are destined to be apart forever. However, the same magic that turned Jenna into a 30-year-old turns her back into her teenage self, and she has the chance to live her life differently. Jenna and Matt end up together in adulthood, rewarded with the dream life of being married to their bestie.
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Amanda Jones (Lea Thompson) is Keith's (Eric Stoltz) teen dream girl. The only problem is that she is the most popular girl in school, and Keith is an outsider. While Keith plots to win Amanda's love, his best friend Watts (Mary Stuart Masterson) secretly pines for him. But Keith sees the tomboy as just a pal.
Even after Keith and Watts share a kiss – for “practice,” of course – Keith is oblivious. He and Amanda go on a few dates, though they hardly seem like an ideal match. It's Amanda, of all people, who finally clues Keith in to how his best friend really feels. Keith decides to go after Watts instead, and the pair finally locks lips for real.
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In 2011, Hollywood gave us two romantic comedies where friends think that they can have sex with each other without commitment. It didn't work in No Strings Attached. And it doesn't work for Dylan (Justin Timberlake) and Jamie (Mila Kunis) in Friends with Benefits either.
The relationship this time has a somewhat unusual twist: Jamie is a headhunter, attempting to recruit Dylan to a new job in New York City. Their friendship begins naturally from there, and soon evolves to include sex – though feelings get in the way before too long. In a charming touch that's very 2011, Dylan eventually wins Jamie over by staging a flash mob for her in Grand Central Station.
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Grade school best friends turned adult roommates Zack (Seth Rogen) and Miri (Elizabeth Banks) are having trouble paying their bills. After a chance run-in with an adult film star (played with gravelly gusto by Justin Long in an unforgettable cameo alongside erstwhile Superman actor Brandon Routh) at their high school reunion, the pair comes up with a genius idea: make racy movies together to earn extra money.
However, even when sex is performed for cash, it doesn't mean that romantic feelings won't emerge. Perhaps sensing that, Zack and Miri put off filming their own sequence. When it does happen, their encounter is far more romantic than raunchy. That leads to a slew of misunderstandings and hurt feelings between the pair, but after filming wraps, they end up together for real.
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Overweight Chris (Ryan Reynolds) has always secretly been in love with his childhood best friend Jamie (Amy Smart). He finally confesses his love for her at their high school graduation, but Jamie tells him that she's not interested in him that way.
The friends drift apart, but meet each other again by chance ten years later. Chris is 100 pounds lighter and has become a successful music manager and playboy in Los Angeles. Jamie still lives in their hometown and works as a bartender.
They both battle with getting over the “friend zone” thing. However, one sweet kiss finally seals the deal.
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Reality Bites is Generation X on steroids. Slacker Troy (Ethan Hawke) and his longtime BFF, class valedictorian Lelaina (Winona Ryder), had one night of drunk passion in their past that resulted in years of unresolved feelings. Now recently graduated from college, they live together with two roommates and do their best to scrape together money to pay the rent.
Laney meets and starts to date Michael (Ben Stiller who also directed the movie), a successful video executive who promises to help her with her career ambitions to be a documentary filmmaker. Michael is the opposite of Troy – stable, dependable, and maybe even a little bit square – and offers Laney an opportunity to have an adult relationship. But that all goes down the drain when Michael helps her sell her documentary, only to edit it into something commercial and hollow.
A heartbroken Laney turns to Troy for comfort. They have a few more hurdles to jump – including the death of Troy's father – but ultimately figure out what's most important. Troy finally commits to Laney, and the two are going to make a go of it as the credits roll.
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Wouldn't life be great if two attractive best friends could also hook up whenever they want? Emma (Natalie Portman) and Adam (Ashton Kutcher) think they can handle the whole “friends with benefits” experiment like so many have tried before them.
However, intimacy eventually leads to actual feelings. There is no such thing as “no strings attached” when it comes to sex, especially not in a romantic comedy. Though Emma initially resists falling for Adam, and Adam refuses to continue their casual arrangement, the two eventually come to an understanding. The ultimate sign of their newfound commitment? Sharing breakfast together.
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Tom (Patrick Dempsey), a wealthy womanizer, and Hannah (Michelle Monaghan) are best friends, and have been since a costumed meet-cute in college. When Michelle travels to Scotland for work, Tom's life feels empty, and he suddenly realizes that he's in love with her. However, Hannah has met a sweet Scottish man named Colin (Kevin McKidd) and agreed to get married. She asks Tom to be her maid of honor.
Tom sets out a plan to sabotage their Scottish wedding. Plenty of highjinks ensue, including a spin on the Highland Games, a tradition involving giving out kisses, and a madcap horseback ride. In the end, Tom confesses his feelings to Hannah, and poor Colin is abandoned at the altar. He at least gets one solid punch in before the happy couple returns to the United States.
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Win a Date with Tad Hamilton!
Photo: DreamWorks PicturesPete (Topher Grace) is hopelessly in love with his best friend Rosalee (Kate Bosworth), though she's oblivious. Rosalee is a small-town West Virginia girl with a massive celebrity crush on the ridiculously handsome actor Tad Hamilton (Josh Duhamel). In real life, though, Tad is worlds away from the charmer he plays on the screen. His image needs a rehabilitation, and fast, so his agent arranges for an over-the-top publicity stunt. Average fans will have the chance to win a date with Tad, with the proceeds benefitting charity.
Rosalee, naturally, wins that date with Tad. Although things start out on an awkward note, he falls for the small-town girl with the big heart. The positive experience makes Tad realize what he's been missing out on in Hollywood. Tad even wins Rosalee over by using Pete's “six smiles” guide to figure out her emotions.
A heartbroken Pete attempts to stop their romance. However, it's Rosalee who finally figures out that Tad is just an actor with LaLa Land on his mind. Pete knows who she is and loves her no matter what.
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Wedding season can be a more difficult time to be single than the holidays. It's no wonder lonely college pals Ben (Jack Quaid) and Alice (Maya Erskine) make a pact to be the other's plus one to the ten weddings that they are collectively invited to that season. It's their way to survive the questioning glare of their friends.
Since weddings are always romantic – even the insufferable ones – Ben and Alice eventually realize that there is more than just friendship between them. They strike up a relationship, and despite a few roadblocks, end the film happily together.
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In this '90s teen update of Cyrano de Bergerac, nerdy Ryan (Shane West) plans a switcheroo with high school cool guy Chris (James Franco). Ryan introduces Chris to his best friend Maggie (Marla Sokoloff) and Chris introduces Ryan to high school “It” girl Ashley (Jodi Lyn O'Keefe). Ryan helps the jock win over Maggie; in return, Chris helps Ryan with Ashley.
The plan slowly starts to work… until Ryan realizes that he has feelings for Maggie. Ashley wasn't his dream girl after all. And after some shenanigans at the prom, Ryan and Maggie are able to confess their true feelings and share a kiss.
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Single All the Way became Netflix's first same-sex romantic comedy in 2021. Los Angeles resident Peter (Michael Urie) asks his best friend and roommate Nick (Philemon Chambers) to pretend to be his boyfriend while he goes to see his family in New Hampshire over the holidays.
While in New Hampshire, Peter begins to develop feelings for Nick despite his mom trying to set him up with her personal trainer. Peter finally confesses, but Nick doesn't want to risk losing their friendship.
In the end, Nick does something amazingly sweet for Peter: he rents out a space for him to open the plant shop of his dreams. They confess their love for each other, and set out to embark on a New England lifestyle together.
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