Although all of these movies are great to watch, they're kind of depressing when you watch them with your boyfriend or girlfriend. This is because the two main love interests either don't actually end up together or aren't happy together, and it's sad to watch it play out - especially when you're with your S/O.
1. "La La Land"
This movie has such a bittersweet ending! You watch it the entire time thinking "how romantic," and then BAM! They break up because of her career, she becomes wildly famous, marries another man, and has a kid with him!! Granted, Seb got to live out his dream of opening up his own jazz club just like Mia lived out her fantasy, but it's still so sad that they never end up together.
2. "The Graduate"
Okay, so the scene where he runs up to her wedding and crashes it and they run away together is SO ROMANTIC. But the ending? Not so much. As their smiles and adrenaline fade, the two sit in unhappy-looking silence as a depressing song plays over the movie. Did they do the right thing? Are they actually in love? Did they live happily ever after???
3. "500 Days of Summer"
From the get-go, the narrator of the movie informs the audience that it "is not a love story." However, the audience, just like the optimistic male lead, believes differently. We come to realize that it's not to be once the female reveals that she doesn't love him and never has...then marries someone else. The movie ends on a positive note, but it's still heart-wrenching to watch such a rocky romance play out.
This is a classic. I really, really believed that Rick and Ilsa would end up together. I mean, they loved each other! Ilsa was literally supposed to stay with Rick, until the plot twist at the end. But Ilsa had another love before Rick, her husband - so she was obligated to him first before anything else.
5. "Gone with the Wind"
This is a classic romance movie and has tons of romantic elements, but as the movie progresses, all hope is nearly lost for Scarlet and Rhett to end up together. Scarlet rejects Rhett, marries another man, and has a life with him. Later, however, she decides she would be happier with Rhett. So in a last-ditch effort, she goes back to him and declares her love in hopes of reuniting with him. However, this time HE denies her with the famous line "Frankly, my dear, I don't give a damn." WOW.