22 Must-Watch Movies Where Best Friends Fall in Love

First comes friendship, then comes love

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We’ll admit, the friends-to-lovers storyline is one of the most common romantic tropes out there. We’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 we’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 22 must-watch movies where best friends fall in love.

75 of the Best Romantic Movies of All Time

1. 13 Going On 30 (2004)

  • Cast: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis
  • Rating: PG-13

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. When they start to spend time with each other, sparks fly.

2. Always Be My Maybe (2019)

  • Cast: Ali Wong, Randall Park, Keanu Reeves, James Saito, Michelle Buteau, Vivian Bang
  • Rating: PG-13

Childhood best friends Marcus and Sasha drift apart after having an awkward hookup as teenagers. But when they cross paths again 16 years later, they reconnect and start over, all while trying to ignore the awkward romantic tension.

3. When Harry Met Sally (1989)

  • Cast: Billy Crystal, Meg Ryan, Carrie Fisher
  • Rating: R

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.

4. Love & Basketball (2000)

  • Cast: Omar Epps, Sanaa Lathan
  • Rating: 16+

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.

5. Brown Sugar (2002)

  • Cast: Taye Diggs, Sanaa Lathan, Queen Latifah
  • Rating: PG-13

Growing up, best friends Andre and Sidney have always shared a passion for hip-hop. But now that they’re adults and taking the industry by storm, it appears that there’s more to their tight-knit friendship than they realized. Especially since their romances with other people never seem to work out.

6. Just Friends(2005)

  • Cast: Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein, Christopher Marquette
  • Rating: PG-13

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.

7. Made Of Honor (2008)

  • Cast: Chris Parson, Patrick Dempsey, Michelle Monaghan
  • Rating: PG-13

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. Can he put an end to Hannah’s wedding?

8. The Duff (2015)

  • Cast: Mae Whitman, Robbie Amell, Bella Thorne, Nick Eversman, Skyler Samue
  • Rating: PG-13

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 start to fall in love.

9. Whatever It Takes (2000)

  • Cast: Shane West, Marla Sokoloff, Jodi Lyn O'Keefe, James Franco
  • Rating: PG-13

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.

10. Love, Rosie (2014)

  • Cast: Lily Collins, Sam Claflin, Christian Cooke
  • Rating: R

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?

11. Plus One (2019)

  • Cast: Maya Erskine, Jack Quaid, Ed Begley Jr.
  • Rating: NR

College BFFs Alice and Ben decide to be one another’s plus-ones as they attend a string of weddings. Their simple agreement turns into an awkward situation when Alice starts to fall hard for Ben.

12. Yesterday (2019)

  • Cast: Himesh Patel, Lily James, Sophia Di Martino
  • Rating: NR

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?

13. Some Kind Of Wonderful (1987)

  • Cast: Eric Stoltz, Mary Stuart Masterson, Craig Sheffer
  • Rating: PG-13

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?

14. Zack And Miri Make A Porno (2008)

  • Cast: Elizabeth Banks, Craig Robinson, Traci Lords
  • Rating: R

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.

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

  • Cast: Kate Bosworth, Topher Grace, Josh Duhamel
  • Rating: PG-13

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.

16. Drive Me Crazy (1999)

  • Cast: Melissa Joan Hart, Adrian Grenier, Susan May Pratt
  • Rating: PG-13

Next door neighbors Nicole and Chase concoct a plan to win their respective crushes by pretending to date. Naturally, a friendship develops, but that quickly turns into something more when they discover there’s chemistry between them.

17. Single All The Way (2021)

  • Cast: Michael Urie Philemon Chambers, Luke Macfarlane, Barry Bostwick
  • Rating: TV-PG

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.

18. What If/the F Word (2014)

  • Cast: Daniel Radcliffe, Zoe Kazan, Megan Park
  • Rating: PG-13

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?

19. No Strings Attached (2011)

  • Cast: Natalie Portman, Ashton Kutcher
  • Rating: R

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.

20. Reality Bites (1994)

  • Cast: Winona Ryder, Ethan Hawke, Ben Stiller
  • Rating: PG-13

Hawke and Ryder are Troy and Lelaina, two good friends and roommates who have never ventured into darting 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.

21. Your Place or Mine (2023)

  • Cast: Reese Witherspoon, Ashton Kutcher, Jesse Williams
  • Rating: PG-13

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.

22. Past Lives (2023)

  • Cast: Greta Lee, Teo Yoo, John Magaro, Choi Won-young
  • Rating: PG-13

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

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