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22 Gen X Movies That Explain All of My Relationship Problems

From High Fidelity to Reality Bites, here are the movies that fed us all the worst advice on love

Collage of movie stills
Everett Collection

I don’t know why I thought rewatching Kevin Smith’s Chasing Amy again would be a good idea. Maybe it’s because it came out 25 years ago, and I’m a sucker for pop culture anniversaries and the misguided notion that movies age like fine wine.

Back in 1997, I thought Chasing Amy was smart and sexy and irreverent — the perfect romantic comedy. But watching it today, with a 50-year-old’s eyes, I’m stunned that I was ever impressed by these doofuses. They mostly sit around, sharing soliloquies about how women don’t understand them. Ben Affleck, with his shellacked pompadour and punchable goatee, is smug and weepy, and his big romantic gesture is offering to have a threeway with his girlfriend and best friend. (“It will be cathartic,” he says with a straight face.)

Honestly, it’s a miracle I managed to convince anyone to marry me, with those kinds of romantic role models. 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 we watched that really messed us up. These were our blueprints for how to act, how to become men that women wanted to be with. With that education, we should all be living alone in cardboard boxes under an overpass.

Here are 22 other movies 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 on my front lawn and blast Peter Gabriel from a boom box until I change my mind.”

Singles (1992)

Terrible Love Lesson: Be a jerk, but a jerk with a soul patch.

Reality Bites (1994)

Terrible Love Lesson: Flirt using passive-aggressive pop culture references while chain-smoking Camel Straights.

St. Elmo’s Fire (1985)

Terrible Love Lesson: Despite your many flaws — not having a job, cheating on her, being really into Woody Allen — she’ll overlook it if you’re always carrying a saxophone.

High Fidelity (2000)

Terrible Love Lesson: She might seem annoyed by your OCD obsessions, but she secretly finds them charming.

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.

Empire Records (1995)

Terrible Love Lesson: If getting into a fistfight at work doesn’t impress her, quit your job to become an artist. Women love guys with unrealistic dreams and no income.

Ferris Bueller’s Day Off (1986)

Terrible Love Lesson: It’s okay to tell elaborate lies to pretty much everyone as long as those lies directly benefit her.

The Empire Strikes Back (1980)

Terrible Love Lesson: Women are attracted to guys with crippling debt and commitment issues.

Before Sunrise (1995)

Terrible Love Lesson: The most meaningful relationships are one-night stands.

Coming to America (1988)

Terrible Love Lesson: Women only want you for your money, so pretend you’re poor at least during the first few dates.

Wayne’s World (1992)

Terrible Love Lesson: Sprinkle your romantic banter with evocative phrases like “monkeys might fly out of my butt.”

Heathers (1988)

Terrible Love Lesson: Convince her that your bad life choices are really her bad life choices.

Clerks (1994)

Terrible Love Lesson: Having sex at work is absolutely a good idea as long as you keep the lights on.

Dazed and Confused (1993)

Terrible Love Lesson: Try to be the least creepy guy in the room. If you’re 10 percent less cringey than the “alright, alright, alright” guy, you’re winning.

Beetlejuice (1988)

Terrible Love Lesson: Goth girls will agree to anything if you’re persistent enough.

Footloose (1984)

Terrible Love Lesson: Angry dancing alone in an abandoned warehouse is in no way disturbing.

Pulp Fiction (1994)

Terrible Love Lesson: A memorable first date needs at least one near-death experience.

Purple Rain (1984)

Terrible Love Lesson: Don’t tell your girlfriend when you’re angry. Instead, write a song about a girl named Nikki with questionable hotel lobby etiquette. That’ll show her.

Clueless (1995)

Terrible Love Lesson: Do not kiss your stepsibling, at least until your parents get divorced.

The Karate Kid (1984)

Terrible Love Lesson: Before you can date someone new, you must first prove your worthiness by defeating her ex-boyfriend in a brutal martial arts championship.

The Matrix (1999)

Terrible Love Lesson: Have complicated emotions that you’re not sure how to express? Just say, “Whoa.” She’ll get it.

Follow Article Topics: Inside-Dope