Decider Lists

Five Years Since ‘500 Days of Summer’: Here are 5 Incredibly Depressing Love Stories to Stream

Today marks the five-year anniversary of 500 Days of Summer,and in honor of the love tale that made you swear off love (for a little while at least), we’ve picked out five equally depressing tearjerkers that prove that love does not always trump all. It dies and leaves us alone with the shades drawn, shoving cookie dough into our mouths like it’s going out of style, and streaming the saddest batch of love stories out there ranked by their Cry Factor. Enjoy!

A Teacher (2013)

Cry Factor:

Up-and-coming indie sweetheart Lindsay Burdge plays Diana Watts, a high school English teacher who has an affair with one of her students and slowly starts to lose control of her life after their relationship draws attention and screeches to a halt. What’s so infuriating is that her love interest, Eric, is literally the worst human being, but she’s too vulnerable and empty to notice. Even though you want to smack her half the time for being so dumb, Diana’s sadness makes you ache for her from the inside-out.

See where you can stream A Teacher on GoWatchIt.

Husbands and Wives (1992)

Cry Factor:

The story of two couples who don’t love each other. Jack and Sally (Sydney Pollack and Judy Davis) decide to break up, which sends close friends Gabe and Judy (Woody Allen and Mia Farrow) for a loop. What if their own relationship isn’t as strong as they originally thought? Turns out it’s not, and they crumble while Jack and Sally decide to give it another shot even though they make each other miserable. Watch this one if you’re feeling especially pessimistic about your future.

See where you can stream Husbands and Wives on GoWatchIt.

Blue Is the Warmest Color (2013)

Cry Factor:

Adèle (Adèle Exarchopoulos) is lost as she goes through the motions of the high school dating scene until she passes Emma, a mysterious, punky, blue-haired artist, on the street and instantly falls for her. What makes this one especially emotional is Adèle’s incredible expressiveness as we watch her heart slowly break as her relationship with Emma runs its course.

See where you can stream Blue is the Warmest Color on GoWatchIt.

Boys Don’t Cry (1999)

Cry Factor: 

What makes the agonizing story of Brandon Teena that much sadder is the fact that it’s true. Brandon (Hilary Swank) is a trans man living in a conservative, unforgiving midwestern town that he’s forced to flee after the truth about his sexuality comes out. In Nebraska, he finds a soulmate in Lana (Chloe Sevigny) who slowly realizes the truth about Brandon, loves him anyway, and does everything she can to try and protect him. If you don’t cry, fine; but if you don’t even feel the urge, it’s quite possible you have no soul.

See where you can stream Boys Don’t Cry on GoWatchIt.

The Broken Circle Breakdown (2012)

Cry Factor: 

Elise and Didier are folk musicians living in Belgium, being super cute and in love, when Elise suddenly gets pregnant. Flash forward to when their adorable little daughter is diagnosed with cancer and, without spoiling too much, the rest of the film follows the couple as they try and cope without turning on each other. Set to a bluegrass soundtrack and featuring some of the most honest on-screen chemistry ever, The Broken Circle Breakdown is almost too real at times. It doesn’t matter who you are or how tough you think you might be, this movie will make you bawl like a baby from start to finish.

See where you can stream The Broken Circle Breakdown on GoWatchIt.