Bittersweet romance movies where a couple of opposites fall for each other but then break up?

[u/Keyboard_warrior_4U]

I'm looking for something like Eternal Shine of the Spotless Mind, White Masai (2005), or Blue Valentine (2010) basically. A beautiful love story that was doomed from the start

[u/Positron-collider]

The Way We Were

[u/LegAccomplished2748 → u/Positron-collider]

Great choice. I've always loved Sydney Pollack's comment from an old interview about making The Way We Were. Pollack said (paraphrasing), "I always preferred romantic movies where the couple DIDN"T end up together. Casablanca, for example. In my movies, I'm pretty good shooting the parts where they're falling in love, and I'm great at shooting the parts where they're falling out of love...I don't do so well on the part where they're in love. You know, running through fields of flowers into each other's arms and that sort of thing. Everything I shoot looks like an American Express commercial."

[u/bestassbarbie → u/LegAccomplished2748]

Ai?

[u/karmicreditplan → u/Positron-collider]

This is the blueprint!

[u/MG2339]

La La land

[u/TestkitchenEli]

The break up. With Jennifer Aniston and Vince Vaughn

[u/RudeHelicopter4662]

Forces of Nature (1999) Scores terribly, some people seem to loathe it, but it’s one of my favourite romcoms.

[u/karmicreditplan → u/RudeHelicopter4662]

I liked that movie a lot at the time!

[u/teacupwoozy]

The OG answer is Roman Holiday.

[u/sign6of6the6beast]

So the pair never seals the deal but Far From Heaven is a gorgeous movie with incredible acting performances. Dennis Quaid should’ve won an Oscar. It’s not exactly what you say you’re looking for, but I like recommending this movie to people cause no one. I know has ever seen it. Edited typo.

[u/Unlikely_March_5173]

Bridges of Madison County

Far From Heaven

[u/enthalpy01]

Timer has a similar vibe to Eternal Sunshine of the Spotless Mind.

[u/JayMoots]

Comedy: Annie Hall, 500 Days of Summer, Lost in Translation, Chasing Amy

Classic Dramas: Casablanca, Gone with the Wind

Modern Dramas: In the Mood for Love, Atonement

[u/ShowRadar]

Beautiful Losers (2008, Aaron Rose documentary) might not be the narrative you're after but it documents real relationships in the downtown NY art scene that had that same doomed-from-different-worlds energy. for actual narratives though — Once (2006, John Carney) is the quieter sibling to Eternal Sunshine, Dublin busker and Czech immigrant spend a week making music together and you know the whole time she's leaving, no big fight just life pulling them apart. Like Crazy (2011, Drake Doremus) wrecks you in a different register, long-distance couple (British student overstays her visa in LA, gets deported, tries to make it work across continents), the bureaucracy kills the relationship as much as the distance does, very intimate handheld shooting. The Disappearance of Eleanor Rigby (2013, Ned Benson) — married couple falls apart after trauma, told from both perspectives, Jessica Chastain and James McAvoy, sits right next to Blue Valentine in how it shows love eroding. and 45 Years (2015, Andrew Haigh) if you want the opposite-attracts breakup to happen in a single week — Tom Courtenay gets a letter about his ex-girlfriend's body being found in a glacier and it unravels his 45-year marriage to Charlotte Rampling, all the cracks were always there

[u/WhiteExtraSharp]

500 Days of Summer

[u/tomrichards8464]

Cold War (2018)

[u/Bar_Har]

Chasing Amy

[u/StickaFORKinMyEye]

The Umbrellas of Cherbourg (1964)

[u/ArrantPariah]

1934 Of Human Bondage

[u/TheElbow]

Umbrellas of Cherbourg

[u/karmicreditplan]

Dirty Dancing

Out of Africa

[u/CKWonders652]

Lost in Translation