25 Must-Watch Movies Where Best Friends Fall in Love, from ‘Brown Sugar’ to ‘Love, Rosie’

I’ll admit, the friends-to-lovers storyline is one of the most common romantic tropes out there. I’ve seen famous pairs like Harry and Sally explore the possibility of men and women being platonic friends, while others like Marcus and Sasha discovered that going from a friendship to a steamy romance can be seriously complicated. Still, there’s something endearing about watching these characters navigate their newfound romantic chemistry—especially since I’ve seen these scenarios play out in real life.

From ’90s classics like Reality Bites to romantic comedies like Always Be My Maybe, keep reading for 25 must-watch movies where best friends fall in love.

1. 13 Going On 30 (2004)

• Cast: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis
• Rating: PG-13
• Director: Gary Winick
• Run Time: 98 minutes

Oh, to be "30, flirty and thriving." In this classic rom-com, Garner lights up the screen as Jenna, a 13-year-old who wakes up in her adult body and realizes that she and her BFF, Matty, have grown apart. To make matters worse, he’s engaged to someone else...but when they start to spend time with each other, sparks fly. I could go on for days about Garner's irresistible charm and her effortless chemistry with Ruffalo. But I especially love how it tackles themes like peer pressure, self-acceptance and friendship.

2. Always Be My Maybe (2019)

• Cast: Ali Wong, Randall Park, Keanu Reeves, James Saito, Michelle Buteau, Vivian Bang
• Rating: PG-13
• Director: Nahnatchka Khan
• Run Time: 102 minutes

Childhood best friends Marcus and Sasha drift apart after having an awkward hookup as teenagers.  But when they reconnect 16 years later, they attempt to bring back their friendship, all while trying to ignore the romantic tension between them. Thanks to the charming cast and laugh-out-loud humor, the movie boasts 90 percent on the Tomatometer, and Wong scored a People's Choice Award nomination for Comedy Movie Star of 2019.

3. When Harry Met Sally (1989)

• Cast: Billy Crystal, Meg Ryan, Carrie Fisher
• Rating: R
• Director: Rob Reiner
• Run Time: 95 minutes

Okay, so maybe Harry and Sally aren’t “best friends,” but their chemistry and intense debates sure make it feel that way. After graduating from college, the pair engage in a heated discussion about whether men and women can be just friends. Years after they part ways, they have a chance encounter that leads to a deeper relationship. The movie earned five Golden Globe nominations, and Nora Ephron an Academy Award nomination for Best Original Screenplay.

4. Love & Basketball (2000)

• Cast: Omar Epps, Sanaa Lathan
• Rating: 16+
• Director: Gina Prince-Bythewood
• Run Time: 127 minutes

Aspiring pro-athletes Quincy and Monica start out as childhood besties, but as they grow older, their friendship slowly blossoms into romance. The only problem? Their demanding careers might threaten their chances of making this relationship work. Now, I'm a sucker for romantic storylines, but this cult classic also does a great job of portraying women's sports. Lathan earned an NAACP Image Award and a BET Award for her incredible performance.

5. Brown Sugar (2002)

• Cast: Taye Diggs, Sanaa Lathan, Queen Latifah
• Rating: PG-13
• Director: Rick Famuyiwa
• Run Time: 109 minutes

Growing up, best friends Andre and Sidney have always shared a passion for hip-hop. But now that they’re adults who are taking the industry by storm, it appears there’s more to their tight-knit friendship than they realized. Especially since their romances with other people never seem to work out. I should note that hip-hop fans are in for a treat with the soundtrack, and the chemistry between the leads is unmatched. It comes as no surprise that it was nominated for seven NAACP Image Awards, including Outstanding Motion Picture.

6. Just Friends (2005)

• Cast: Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein, Christopher Marquette
• Rating: PG-13
• Director: Roger Kumble
• Run Time: 94 minutes

Ten years after losing touch with his high school BFF, whom he was secretly in love with, Chris has the ultimate glow-up and reunites with his partner in crime, determined to win her heart this time around. Yes, it's predictable, but Ryan Reynolds’s performance is pure gold. And if you've ever struggled with unrequited love, this one's for you.

While discussing his inspiration for the movie, filmmaker Adam “Tex” Davis told AV Club, "I was in a two-year 'just friends' relationship with a girl in college. I really thought I had a shot, you know, but she was dating this other guy who was much older. And I’m like, 'She’s going to get tired of this guy. He might be the president now, but I’m the vice president. When he gets assassinated or impeached, I’m going to take office and it’s going to be great.' And it just never happened."

7. Made Of Honor (2008)

• Cast: Chris Parson, Patrick Dempsey, Michelle Monaghan
• Rating: PG-13
• Director: Paul Weiland
• Run Time: 101 minutes

In this gender-swapped version of My Best Friend’s Wedding, Tom comes to realize that his feelings for his best friend, Hannah, run deeper than he originally thought. The problem? She’s marrying a charming Scotsman, and to make matters worse, he’s the best man. So, can he put an end to Hannah’s wedding? While critics weren't too fond of the rom-com, it was a box-office success, earning $106.4 million worldwide. (Oh, and did I mention that McDreamy Dempsey shot a nude locker room scene that ended up getting cut?)

8. The Duff (2015)

• Cast: Mae Whitman, Robbie Amell, Bella Thorne, Nick Eversman, Skyler Samue
• Rating: PG-13
• Director: Ari Sandel
• Run Time: 101 minutes

Loved Easy A? Allow me to introduce The Duff. After learning that most of her peers have dubbed her the “designated ugly fat friend” in her clique of BFFs, high school senior Bianca enlists the help of her childhood friend and popular jock, Wesley, to reinvent herself. As they spend more time together, they—you guessed it—start to fall in love. (P.S., I may or may not have developed a crush on Amell after watching this...)

9. Whatever It Takes (2000)

• Cast: Shane West, Marla Sokoloff, Jodi Lyn O'Keefe, James Franco
• Rating: PG-13
• Director: David Raynr
• Run Time: 94 minutes

Ryan, a nerdy high schooler, agrees to help the school’s star athlete win the heart of his best friend, Maggie, in exchange for an introduction to the most popular girl in school. It doesn’t take long for Ryan to realize that he may be pursuing the wrong girl. This modernized version of Edmond Rostand's 1897 play, Cyrano de Bergerac, was Aaron Paul's film debut.

10. Love, Rosie (2014)

• Cast: Lily Collins, Sam Claflin, Christian Cooke
• Rating: R
• Director: Christian Ditter
• Run Time: 102 minutes

Alex impulsively kisses his childhood BFF at her 18th birthday party and realizes that he has romantic feelings for her. But when she vaguely tells him the next day that she wishes the night didn’t happen, he takes it as rejection. The duo are separated when Alex moves to America, which proves to be a challenge for them. Can their friendship survive time and distance? Or even better, turn into romance? The movie is based on Cecelia Ahern's novel, Rosie Dunne (also called Where Rainbows End in Ireland), which spans 45 years, while the movie is set over 12 years.

11. Plus One (2019)

• Cast: Maya Erskine, Jack Quaid, Ed Begley Jr.
• Rating: NR
• Director: Jeff Chan, Andrew Rhymer
• Run Time: 98 minutes

College BFFs Alice and Ben decide to be each other's plus-ones for a string of upcoming weddings. Their simple agreement turns into an awkward situation when Alice starts to fall hard for Ben. The storyline doesn't feel formulaic and the leads are phenomenal, but I especially appreciate the thoughtful one-liners. Like when Ben says, "If you spend your whole life looking for perfect, you wind up with nothing."

12. Yesterday (2019)

• Cast: Himesh Patel, Lily James, Sophia Di Martino
• Rating: NR
• Director: Danny Boyle
• Run Time: 116 minutes

Jack Malik is on the fast track to wealth and fame as he sets out to re-introduce the world to music by The Beatles. But while his career is thriving, his love life isn’t so dazzling. When his best friend professes her love to him, it puts a strain on their relationship. But can they recover from it? (Psst, expect to see a quick cameo of Ed Sheeran's wife on his private jet.)

13. Some Kind Of Wonderful (1987)

• Cast: Eric Stoltz, Lea Thompson, Mary Stuart Masterson, Craig Sheffer
• Rating: PG-13
• Director: Howard Deutch
• Run Time: 95 minutes

Keith never saw his best friend, Watts, in a romantic way—thanks in part to her tomboy style. But that changes when he starts to date the most popular girl in school and enlists the help of Watts. Did Keith go after the wrong girl? Molly Ringwald was offered the role of Amanda Jones, and Lea Thompson originally didn't take the part, but she then accepted the role after working on Howard the Duck.

14. Zack And Miri Make A Porno (2008)

• Cast: Elizabeth Banks, Craig Robinson, Traci Lords
• Rating: R
• Director: Kevin Smith
• Run Time: 102 minutes

Desperate to make ends meet, two broke best friends, Zack and Miri, resort to making porn movies together. Initially, they agree to not let sex change the nature of their relationship, but over time, they start to catch feelings for each other. BTW, per IMDB, the f-word is said a whopping 229 times.

15. Win A Date With Tad Hamilton! (2004)

• Cast: Kate Bosworth, Topher Grace, Josh Duhamel
• Rating: PG-13
• Director: Robert Luketic
• Run Time: 96 minutes

Rosalee, a young store worker, is thrilled to learn that she won a date with a celebrity named Tad Hamilton. Her best friend, Pete, is bummed beyond belief. A love triangle forms as both Tad and Pete go out of their way to win her heart—but for very different reasons. Fun fact: Josh Lucas was offered the role of Tad, but he turned it down.

16. Drive Me Crazy (1999)

• Cast: Melissa Joan Hart, Adrian Grenier, Susan May Pratt
• Rating: PG-13
• Director: John Schultz
• Run Time: 91 minutes

Next-door neighbors Nicole and Chase concoct a plan to win their respective crushes over by pretending to date. Naturally, a friendship develops, but that quickly turns into something more when they discover there’s chemistry between them. The nostalgic classic was originally called Next to You, but was renamed after Britney Spears's hit song, "(You Drive Me) Crazy," after it was included on the soundtrack. Both Hart and Grenier appeared in the music video.

17. Single All The Way (2021)

• Cast: Michael Urie Philemon Chambers, Luke Macfarlane, Barry Bostwick
• Rating: TV-PG
• Director: Michael Mayer
• Run Time: 101 minutes

Netflix's first gay rom-com follows Peter, a social media strategist who finds himself in a bit of a pickle when he learns that his boyfriend is married. Feeling desperate, he asks his best friend, Nick, to travel back home with him for the holidays and pretend to be his boyfriend. However, his mom has other plans. Editor Joel Calfee says, "If there's one brand that Single All the Way feels akin to, it is clearly Hallmark Christmas movies. The film includes the same story structure and cheesy dialogue as Hallmark classics, but Christmas rom-com fans will be glad this is the case." The Netflix comedy won a GLAAD Media Award for Outstanding TV Movie.

18. What If/the F Word (2014)

• Cast: Daniel Radcliffe, Zoe Kazan, Megan Park
• Rating: PG-13
• Director: Michael Dowse
• Run Time: 102 minutes

Wallace, a med-school dropout, has survived a few failed relationships—but he’s not prepared to deal with another, so he gives up on looking for the one. That is, until he meets the charming Chantry. Unfortunately for him, she already has a boyfriend, so he immediately gets friend-zoned. Can he turn their close friendship into something more?

The filmmakers originally cast Casey Affleck and Mary Elizabeth Winstead as the leads, but they had a change of heart and went with Kazan and Radcliffe.

19. No Strings Attached (2011)

• Cast: Natalie Portman, Ashton Kutcher
• Rating: R
• Director: Ivan Reitman
• Run Time: 108 minutes

Can a friends-with-benefits relationship really work? Perhaps it can for some, but that’s certainly not the case for Emma and Adam. When these two friends agree to sleep with each other with “no strings attached,” they quickly learn that adding sex to the equation can seriously complicate things…and ultimately lead to romantic feelings. As it turns out, the comedy went through quite a few title changes. Per IMDB, the initial title was F**k Buddies, then Friends with Benefits. And at the last minute, the final choices were Hooking Up and No Strings Attached.

20. Reality Bites (1994)

• Cast: Winona Ryder, Ethan Hawke, Ben Stiller
• Rating: PG-13
• Director: Ben Stiller
• Run Time: 99 minutes

Hawke and Ryder are Troy and Lelaina, two good friends and roommates who have never ventured into dating territory, despite their mutual attraction. But after they sleep together, they have a messy confrontation that prompts Troy to run away—until a devastating event forces him to reevaluate his choices. FYI, this marked Ben Stiller's feature directorial debut and Renée Zellweger's theatrical movie debut.

• Cast: Reese Witherspoon, Ashton Kutcher, Jesse Williams
• Rating: PG-13
• Director: Aline Brosh McKenna
• Run Time: 111 minutes

Twenty years after having a one-night stand, Debbie (Witherspoon) and Peter (Kutcher) have remained best friends. One day, they decide to swap houses to mix up their daily routine. But they soon discover what's been missing from their lives all along. In his review, Calfee wrote, "Aline Brosh McKenna pens another winning rom-com, which boasts strong female characters, richly-developed dynamics and jokes-a-plenty." The film was a box office success and grossed over $214 million.

• Cast: Greta Lee, Teo Yoo, John Magaro, Choi Won-young
• Rating: PG-13
• Director: Celine Song
• Run Time: 106 minutes

Nora and Hae Sung, who were childhood best friends turned lovers, who reunite after being separated two decades ago. Now adults, they meet in New York City and spend a week together. During that fateful week, they confront themes of love, destiny and their decisions in life.

In her review, Associate SEO Editor Marissa Wu wrote, "Past Lives is a universal human story. It’s about ambition, sacrifice, regret, fate, entertaining 'what could have been,' being OK with the choices you’ve made and letting go of the temptation to throw away the life you have now for the one you think you might have wanted." Past Lives is inspired by Song's life, and it earned two Oscar nominations for Best Original Screenplay and Best Picture.

• Cast: Madeline Carroll, Callan McAuliffe, Rebecca De Mornay, Anthony Edwards
• Rating: PG-13
• Director: Rob Reiner
• Run Time: 90 minutes

If you enjoy coming-of-age flicks that honestly portray the adolescent experience, then you'll love Flipped. Based on Wendelin Van Draanen's novel of the same name, the rom-com follows Juli and Bryce, two eighth-grade BFFs who have opposite personalities. Juli is head over heels for Bryce, but he doesn't reciprocate those feelings. That is, until Juli finally moves on and agrees they're better off as friends. It's easily one of the cutest movies about best friends who fall in love.

• Cast: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett
• Rating: PG-13
• Director: P. J. Hogan
• Run Time: 104 minutes

Things can get rather complicated with BFFs of the opposite sex when love interests are involved—especially when other love interests are involved. This classic film follows Julianne Potter, a food critic who realizes she’s in love with her best friend, Michael, after he tells her he's about to get married to his girlfriend in a few days. Thinking she may still have a chance of winning him over, Julianne plots to ruin the wedding, but chaos ensues. The characters are seriously problematic, but you'll appreciate the humor.

• Cast: Adam Sandler Jennifer Aniston, Nicole Kidman, Nick Swardson
• Rating: PG-13
• Director: Dennis Dugan
• Run Time: 117 minutes

If you loved watching the dynamic duo as married detectives in Murder Mystery, you'll get a kick out of this rom-com. Here, Aniston plays the loyal friend and employee of her boss, Danny. When Danny meets the woman of his dreams, he tries to pursue her, but his plan doesn't work because he's trying to live up to a lie. So, to win the girl, he enlists the help of his trusty assistant. Despite the low Tomatometer score, the movie was a big success with fans, earning $215 million at the box office.

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