Engaging in romantic relationships with friends can lead to complications. However, a little chaos can be entertaining! Transform your everyday life into a cinematic experience by unexpectedly proposing to your close friend! What could possibly misfire? In these top 10 films showcasing friendships that evolve into romance, everything ultimately aligns perfectly. Life certainly reflects art, right?
10. Nick & Nora’s Infinite Playlist (2008)

If your best friend is an indie music fan, you’ll want to introduce them to Peter Sollett’s Nick & Nora’s Infinite Playlist! The story follows Nick, a melancholic bassist, and Nora, a quirky music enthusiast, who join forces one night in New York City to find a secret concert by their favorite band. As they inch closer to their destination, sparks begin to fly. For those who enjoy cozying up to The Strokes’ music (because someone has to) this film is a must-see.
9. One Day (2011)

Lone Scherfig’s One Day unfolds as an intense slow burn over the span of decades. Friends Emma and Dexter keep a yearly tradition alive, meeting each year on the anniversary of their graduation. No matter where life leads them, they find a way back to one another. Friends forever, right? Over the years, their platonic bond makes a gradual transition into something deeper. While their classmates might have predicted this shift, the duo is left blissfully unaware until it’s too late.
8. Brown Sugar (2002)

Rick Famuyiwa’s Brown Sugar narrates the journey of two friends whose shared passion for hip hop brings them together from childhood. As Sidney and Dre chase their dreams in the music industry, they can’t shake the feeling that their respective partners aren’t the right match. They soon realize that the best melodies are created when they’re together, though it takes them a good while to come to that conclusion.
7. Always Be My Maybe (2019)

Have you ever felt like your childhood friend has outshined you? Nahnatchka Khan and Ali Wong’s Always Be My Maybe perfectly captures the whimsy of rekindled friendships. Sasha, a celebrity chef, reconnects with Marcus, who leads a simpler life. Despite their starkly different lifestyles, nostalgia pulls them into a reconnection, leading them to contemplate that their best days may still lie ahead—together. Both have secretly harbored feelings, but timing isn’t everything.
6. But I’m A Cheerleader (1999)

In Jamie Babbit’s comedic romp, But I’m A Cheerleader, we follow the story of teenager Megan, who, after her parents suspect she’s gay, gets sent to a conversion therapy camp. Although the premise sounds serious, there’s a humorous twist. At the camp, she meets Graham and forms a romantic connection with her fellow attendees, challenging the very reasons she was sent there. Yes, Harold, they actually are lesbians.
5. A Walk To Remember (2002)

With this entry, we’ve crossed into Nicholas Sparks territory. Adam Shankman’s adaptation of Sparks’ novel introduces us to Jaime, a rebellious young man, and Laura, a sweet preacher’s daughter. Their worlds unexpectedly collide and create a bond that evolves into love, only to face the heartbreak that oft accompanies Sparks’ narratives. A black hole may be less damaging to the heart.
4. Holding The Man (2015)

Neil Armfield’s Holding The Man draws from Timothy Conigrave’s poignant memoir chronicling his beautiful yet heartbreaking 15-year love story with a schoolmate at an all-boys institution in the 1970s. A decade known for hostility towards gay individuals, the narrative unfolds during a time of intense societal challenges. If you believe Sparks’ tales are tear-jerkers, brace yourself; this film will shatter your heart into pieces, then compel you to watch again.
3. Rafiki (2018)

Wanuri Kahiu’s Rafiki tells the story of two women in Kenya whose fathers find themselves on opposing sides of the nation’s political landscape. In a contemporary twist on a classic tale of forbidden love, the duo must navigate the challenges of their “illegal”relationship in a country that struggles with acceptance. While the film contains difficult themes of intolerance, it ultimately shines as a story of resilience and love’s triumph over adversity.
2. Silver Linings Playbook (2012)

Silver Linings Playbook highlights the resilience of love, proving that it can flourish in even the darkest circumstances. David O. Russell’s film follows Pat, who grapples with bipolar disorder, and Tiffany, who is coping with personal loss. Through their shared journey toward healing, they slowly forge a bond that blossoms into something special, emphasizing how their challenges ultimately draw them closer together.
1. When Harry Met Sally (1989)

Rob Reiner’s When Harry Met Sally has undeniably earned its place as an iconic film, probing the age-old debate of whether men and women can maintain a purely platonic friendship. Though many can, Harry and Sally’s connection tells a different story. Their journey from acquaintances to close friends gradually evolves into deeper feelings, subverting the notion that staying just friends is easy—especially during memorable moments like witnessing a fake orgasm in a crowded diner, which is essentially the foundation of true love.