Columbia Pictures
In real life and the movies, best friends fall in love all the time. No matter how they go from platonic to romantic, nothing is sweeter than a “they didn’t know until they knew” scenario. That’s why it’s such a foolproof formula.
The truth is, I can’t get enough of a good rom-com, but I also love a really bad one. Even when the story is implausible, the script falls flat, and the “best friends” manipulate each other for 90% of the movie, I’m still rooting for them.
But while love may be blind, I am not. As badly as I want to, I can’t turn a blind eye to just how bad some of these really are. So from the oh-so-sweet to the incredibly sour, here are some of the best and worst movies about falling in love with your best friend, ranked.
After “one hot month” in college, Julianne Potter (Julia Roberts) and Michael O’Neal (Dermot Mulroney) remain best friends, making a pact to marry if they’re still single by 28. Four days before her 28th birthday, Michael calls to say he’s marrying the purely perfect 20-year-old, Kimberly (Cameron Diaz). The nerve!
Stricken by sudden jealously and shock, Julianne goes out of her way to sabotage the pending nuptials, made all the more complicated when Michael’s bride-to-be asks her to be the maid of honor.
My Best Friends Wedding is not your average romantic comedy. This modern love story about realizing you’re in love with your best friend a little too late is refreshingly bittersweet and surprisingly subversive for its genre.
Aside from Rupert Everett’s impromptu musical number at a seafood restaurant, much of what transpires also feels true to life.
What happens in No Strings Attached is all-too-obvious, but that’s okay. In this Hollywood rom-com starring Natalie Portman and Ashton Kutcher, depth is hardly the point.
But looking at the friends to lovers journey rather than its predictable destination, it still falls flat.
Even with so much star power and undeniable potential, this movie about BFFs failing at their agreement to “use each other just for sex” is overwhelmingly average.
Or as The Rotten Tomatoes Critics Consensus puts it, “it benefits from the presence of Natalie Portman and director Ivan Reitman’s steady hand, but No Strings Attached doesn’t have the courage or conviction to follow through on its ribald premise.”
All’s fair in Love & Basketball. Painful and poignant, Sanaa Lathan and Omar Epps star as an on-and-off couple who’ve developed a bond throughout their lives.
They share a passion for the game and a passion for each other, but they’re inevitably forced to choose what matters most.
This award-winning movie gives an insightful look at the relationship between two childhood friends who grow up to be promising athletes and lovers. While masterfully wrestling with complex identity issues, Love & Basketball carves out a timeless love story that continues to persevere.
Since they were kids, Chris Brander (Ryan Reynolds) has been hopelessly in love with his best friend Jamie Palamino (Amy Smart). But when he was about 100 pounds heavier and had braces, Chris felt Jamie was eternally out of his league.
When he finally musters up the courage to confess his feelings, things don’t go as hoped. Inevitably, Jamie tells Chris she loves him but adds “like a brother.” He’s crushed. Ten years after being friend-zoned, everything changes.
In this quintessentially shallow rom-com, Chris is “a different person” when they inevitably reunite over the holidays. He’s more confident, good with the ladies, and has a six-pack. Now undeniably handsome, Chris thinks he has what it takes to win over the object of his unreciprocated affection.
If Just Friends was funnier, perhaps it wouldn’t feel so cringy.
There’s a lot going on in this coming-of-age story with a twist, but Juno is pulled by the quiet undertow of the central romance from start to finish.
When a precocious teenager convinces her best friend into “a little experimenting,” she winds up pregnant. While Juno faces tough issues “far beyond her maturity level,” she pushes Bleeker, her BFF, away. But ultimately, she realizes she’s “totally in love” with him.
The Rotten Tomatoes Critics Consensus called this award-winning flick, “one of the brightest, funniest comedies” to date thanks to its “smart script, direction, and assured performances.” Quick-witted and uniquely touching, it’s hard not to fall in love with Juno.
In a classic mixup, two high school guys from vastly different social circles help each other pursue two very different girls, gradually realizing they’re going after the wrong one.
Sweet, accordion-playing Ryan Woodman (Shane West) has a whopping crush on It Girl Ashley Grant (Jodi Lyn O’Keefe), but she barely knows he’s alive. Chris Campbell (James Franco) is a hot jock with his eye on Ryan’s brainy and beautiful BFF/next-door neighbor, Maggie Carter (Marla Sokoloff).
This run-of-the-mill teen rom-com does everything you’d expect it to, except make you laugh much. And maybe it’s just me, but the girls too quickly agree to a partner swap after all the manipulation.
Directed by Nora Ephron, this charming flick stars 90s darlings Tom Hanks and Meg Ryan. Oh so timely (for its time), these friends turned lovers develop an intimate and close online relationship but keep their identities anonymous. Blissfully oblivious, they’re actually mortal enemies in real life.
Kate runs a local bookstore with a rich history and Joe is putting her out of business with his gigantic book emporium. He figures out their conundrum first and tries to reconcile his mixed-up feelings, then fully falls in love with his rival/closest confidante. In a nutshell, love conquers capitalism.
Obviously, You’ve Got Mail is no Sleepless in Seattle, but it has some magical moments, clever one-liners, and that timelessly classic Hanks-Ryan chemistry.
Friends With Kids is daringly honest, insightful, and the cast was pretty dang solid. Frankly, it’s not a bad flick. But this rom-com was not very romantic, especially when it tried to be. Perhaps that’s why reviews are consistently split down the middle.
Julie (Jennifer Westfeldt) and Jason (Adam Scott) are best friends. With biological clocks ticking, they decide if they want kids it’s “now or never,” but they’re also single. Luckily, they have each other. They decide to conceive a child, co-parent without being a couple, and figure out the rest.
Their less-than-best-laid plan works for a while, but Julie soon realizes she’s in love with Jason. Jason is busy dating MJ (Megan Fox) so it takes him longer.
Repelled by the idea of being with his best friend, Jason describes her as “an extra limb.” When Julie tearfully confesses her feelings, Jason says he’s not attracted to her. She cries, and cries, and cries. After growing bored of his objectively hot girlfriend (whom he thought he loved), Jason decides Julie is actually the one. Or she could be. How…romantic?
13 Going on 30 is one of those lighthearted rom-com comfort foods that’s easy to emotionally digest. But if I’m being really honest, there’s something very off about the “best friend turned lovers” story within.
Thanks to some magic fairy dust and 17 years, Jenna Rink (Jennifer Garner) realizes she’s in love with her childhood best friend, Matty (Mark Ruffalo). As adults, they’re no longer friends, which shocks and shakes Jenna to the core.
The last time she saw Matty, she told him she never wanted to see him again. Immediately after her 13th birthday, she wakes up “thirty, flirty, and thriving”, and hunts Matty down. Unfortunately, it appears Jenna isn’t thriving as much as she’d hoped. Matty knows they’re falling in love but he turns Jenna down.
After returning to her childhood home, Jenna wakes up at her thirteenth birthday party. After Matty finds Jenna alone in the closet, they kiss. They end up married seventeen years later.
Sure, there are some plot holes, like the fact that the lead is meant to be an incredibly naive preteen trapped in a 30-year-old woman’s body and falls in love with a grown man. Pretty uncomfortable, tbh.
Some Kind of Wonderful is often considered a pioneer of its genre. In Suburban LA, Keith (Eric Stoltz) and Watts (Mary Stuart Masterson) have grown up as the very best of friends. Bandana-wearing Watts is not your typical girly girl, so Keith is vividly blind to what’s really between them.
As expected, he’s trying to land a date with the most popular girl in school, Amanda (Lea Thompson). His eyes are finally opened after a hot and heavy “practice” kiss with Watts. The rest is romantic movie history.
The Rotten Tomatoes Critics Consensus says, “Some Kind of Wonderful is above-average ’80s teen fare for people who need as much John Hughes in their lives as possible.”
Starring Ali Wong, Randall Park, and Keanu Reeves, this tale of reuniting with “the one who got away” is heartwarming, hilarious, and cleverly layered.
In Always Be My Maybe, the BFFs start out as childhood sweethearts who become way more than friends by their teen years. After completely losing touch, fate brings them back into each other’s lives.
But when they reunite in adulthood, these old flames feel like they’ve become strangers. Not only have they taken very different career paths, but they’re also in new relationships. Still, it seems all too clear to everyone around them that the love they once shared will never die.
I really enjoyed this movie, but it’s undeniably ridiculous. With that said, the acting is great.
Tom (Patrick Dempsey) is a playboy terrified of commitment. Hannah (Michelle Monaghan) is his longtime best friend and the one woman he admittedly needs in his life. The catch? He genuinely cares for her, so dating is off the table. But when Hannah finds “Mr. Right,” Tom realizes he loves her and sets out to prove she’s marrying Mr. Wrong.
Naturally, Hannah makes Tom her Maid of Honor. In turn, he can only do his sabotaging ever-so-manipulatively. He wants the breakup to be her decision. All in the name of love, right?
Now engaged, she sees Tom (and her fiancee) differently but keeps that to herself. Until, of course, their friends and family fly to Scotland for a fairytale wedding. That’s when everything finally becomes crystal clear (and needlessly expensive) for all involved, especially when Patrick Dempsey barges into the church on a horse.
Fresh out of college and unsure of what’s next, an aspiring videographer named Leilana (Winona Ryder) is working on a documentary starring herself and her closest friends. Meanwhile, she has an intense, will-they-won’t-they thing with her brooding and perpetually out-of-work best friend Troy (Ethan Hawke). But he’s obviously in love with her–and that’s where things get complicated.
Terrified of losing each other, they both hesitate to make a move. As their other best friend Vickie (Janeane Garofalo) warns, “sex is the quickest way to ruin a friendship.”
Vividly in denial about their feelings, Laney starts dating a well-meaning yuppie named Michael (Ben Stiller). But one night, these BFFs hold nothing back, changing their relationship forever. Unfortunately, Laney forgot to break up with her boyfriend first, and mutual fears of losing each other reach an all-time high.
Frankly, it doesn’t get more 90s than Reality Bites. The story–and the soundtrack–still holds up!
You’d think these two would’ve learned something from No Strings Attached. But alas, foolish friends once again rush into casually cold agreements about having sex without developing feelings.
There are some truly funny and honest moments in this romantic romp starring Mila Kunis and Justin Timberlake. However, since the premise so closely resembles its underwhelming predecessor (which came out a mere five months earlier), there are quite literally no surprises.
When it comes to movies about falling in love with your best friend, there is perhaps none more iconic (or quotable) than When Harry Met Sally. Beyond that, this timelessly sharp Rob Reiner flick famously set a new standard in the realm of rom coms as a whole.
Starring Billy Crystal and Meg Ryan, this lilting love story unfolds over a ten-year span, much of which is spent with the main characters never thinking of each other “that way.” We also get to hear the touching love stories of other kismet couples who knew when they knew. And amazingly, it never gets cheesy.
Whether you’re an eternal optimist or love’s greatest skeptic, I’d highly recommend watching When Harry Met Sally if you somehow haven’t yet.
