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The films that taught us how to fall in love and immediately screw it up.
Everett Collection (6)
I don’t know why I thought rewatching Kevin Smith’s Chasing Amy again would be a good idea, especially right before Valentine’s Day. Back in 1997, I thought the movie was smart and sexy and irreverent, the kind of romantic comedy that made you feel clever just for liking it.
Watching it now through a 56-year-old’s eyes, I’m stunned that I was ever impressed by these doofuses. They mostly sit around delivering endless monologues about how women don’t understand them. Ben Affleck is smug and weepy, and his big romantic gesture is offering to have a threesome with his girlfriend and best friend. (“It’ll be cathartic,” he says with a straight face.)
If Valentine’s Day has always felt weirdly stressful or vaguely fraudulent, this might be why. The movies we watched growing up didn’t just entertain us, they trained us. Honestly, it’s a miracle I managed to convince anyone to marry me, what with those cinematic role models rattling around in my head. We like to joke about all the useless stuff we learned in high school, like Latin, cursive and the Dewey decimal system. But it’s the movies that really messed us up.
Here are 25 other films that defined us as Gen Xers, and the misguided lessons in love they imparted to us.
Say Anything… (1989)
Terrible love lesson: When she says “no,” maybe what she really means is “show up uninvited outside my house and blast Peter Gabriel from a boom box until I change my mind.”
“Singles” taught us that if you bring a guitar everywhere and dress like laundry day is a lifestyle, emotional availability is optional.
Warner Bros./Courtesy Everett Collection
Singles (1992)
Terrible love lesson: Be a jerk, but a jerk with a soul patch.
“Reality Bites” taught us that Ethan Hawke could hurt Winona Ryder’s feelings repeatedly and still be framed as the right choice.
Universal/Courtesy Everett Collection
Reality Bites (1994)
Terrible love lesson: Flirt using passive-aggressive pop-culture references while chain-smoking Camel Straights.
The Breakfast Club (1985)
Terrible love lesson: The girl you’re attracted to will instantly transform into somebody completely different if you just pressure her enough. Also, a makeover involving a headband is basically marriage material.
St. Elmo’s Fire (1985)
Terrible love lesson: Despite your many flaws — not having a job, cheating on her, never meeting a shirt collar he wouldn’t pop — she’ll overlook it if you’re always carrying a saxophone.
High Fidelity (2000)
Terrible love lesson: She may seem annoyed by your particular interests, but she secretly finds them charming.
“Dirty Dancing” proved that a healthy relationship requires Olympic-level upper-body strength.
Vestron Pictures/Courtesy Everett Collection
Dirty Dancing (1987)
Terrible love lesson: The foundation of a healthy relationship is your ability to catch and support her entire body weight if she suddenly leaps at you.
Fast Times at Ridgemont High (1982)
Terrible love lesson: Romantic gestures are best performed in pool houses owned by other people’s parents.
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