Mandatory Staff Picks: The Best Movies About Unrequited Love
Love is the greatest feeling in the world…unless the one you want doesn’t reciprocate your feelings. Then it’s the worst. Stabbing yourself through the heart with a jagged piece of glass would be preferable to the agonizing, gut-twisting sensation of rejection. You’re not alone in your disappointment, however. Hollywood loves a good unrequited love story, and the movies that tackle this topic do so with uncanny accuracy. While you’re waiting for time to erase the pain inflicted by the one who got away, distract yourself with these movies and thank Cupid you didn’t get it as bad as these characters did.
Mandatory Movies: What To Watch When You’re Tempted To Text Your Ex
'500 Days of Summer'
What do you do when the one you thought burned as intensely about you as you did about her turns out to be lukewarm? You revisit every memory of the relationship, trying to solve the mystery of how you missed all the red flags. That's what Tom (Joseph Gordon-Levitt) does after Summer (Zooey Deschanel) dumps him in what became the golden standard of unrequited love films.
When Mavis Gary (Charlize Theron) receives a birth announcement from her high school sweetheart Buddy Slade (Patrick Wilson), she drops everything to return to her small Minnesota hometown for a visit. She quickly finds that it's going to be harder to rekindle the flame between them than she thought thanks to his wife and new baby.
Photo: Paramount Pictures
This cult classic from Kevin Smith follows Holden McNeil (Ben Affleck), who falls for a fellow comic book artist Alyssa Jones (Joey Lauren Adams). There's just one hitch: she's a lesbian.
'The Great Gatsby'
Jay Gatsby (Leonardo DiCaprio) does everything in his power (OK, mostly throws extravagant parties) to lure his longtime unrequited love, Daisy (Carey Mulligan), across the lake to his house and away from her husband. Spoiler alert: it doesn't quite work as intended.
Newbie (and underage) Rolling Stone reporter William (Patrick Fugit) nabs a gig following the band Stillwater on tour. Along the way, he gets closer to the band's top groupie, Penny Lane (Kate Hudson), but never seals the deal.
You know that saying, "Love the one you're with"? The characters in this film have apparently never heard of it. They're all trying to get with someone else. Willie (Timothy Hutton) is disillusioned with his fiancée, so he flirts with jail bait neighbor Marty (Natalie Portman). Married woman Darian (Lauren Holly) has an affair with her high school sweetheart Tommy (Matt Dillon). And Paul (Michael Rapaport) can't let go of his ex, Jan (Martha Plimpton), who has moved on.
'My Best Friend's Wedding'
When Julianne (Julia Roberts) hears that that her best friend Michael (Dermot Mulroney) is getting married, she's devastated. The duo had a deal: if they both made it to 28 unmarried, they'd get hitched. Now, she hauls ass to Chicago, asks a gay pal to pose as her fiance (Rupert Everett), and tries to sabotage Michael's wedding to Kimberly (Cameron Diaz), all in the name of her love for him. This charming comedy captures the embarrassing lengths we'll go to when love is on the line.
An abandoned human invention, Edward (Johnny Depp), is taken in by a local Avon lady and is immediately smitten with her teenage daughter, Kim (Winona Ryder). Can his love for her overcome the fact that Edward has, well, scissors for hands? (It would certainly make sex complicated...)
Developmentally delayed Forrest Gump (Tom Hanks) first met the love of his life, Jenny (Robin Wright), in childhood. As an adult, he proposes, but she turns him down. She does give him a pity fuck, though, and ends up with an unexpected parting gift.
Finn (Ethan Hawke) has the hots for Estella (Gwyneth Paltrow), who intermittently seduces and rejects him for years before marrying another man. Can you say "masochist"?
'Sleeping With the Enemy'
Laura (Julia Roberts) may have loved Martin (Patrick Bergin) at one point in time (she married him, after all), but he quite literally beat all the love out of her. Now, she's determined to escape his violent clutches by faking her own death and starting over in a new town. Will he be able to let go as easily as she did? This thriller will keep you on the edge of your seat as it all plays out.
'The Hand That Rocks the Cradle'
When Claire (Annabella Sciorra) hires nanny Peyton (Rebecca De Mornay) to help out around the house, she never expected that Peyton would fall for her husband (Matt McCoy), setting off a series of Peyton's brutal schemes to get Claire out of the picture -- permanently.