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There was also a window where "gay" meant "uncool." > 2. (slang, derogatory) Used to express dislike: lame, uncool, stupid. https://en.wiktionary.org/wiki/gay

• noduerme 5y ago
  To teenage boys where I grew up the '90s, "don't be gay" was just a standard egg-on challenge, interchangeable with "don't be a pussy." We weren't exactly in touch with our feminine sides. Your supposed masculinity was proven by doing things more idiotically dangerous than your friends. Only danger could lead to teenage glory. (See: Jackass). We had a saying for it: "Balls and stupidity." Teenage boys are like 2-year-old dogs before they get snipped. Rollerblading just wasn't dangerous enough. Especially with a bunch of pads on. Also, older people started doing it. You'd see lawyers rollerblading to work holding a latte. That more than anything probably killed it for teenagers. After living in Spain and watching teenage boys do mindlessly dangerous moto dirtbike tricks for audiences of girls on the street, I had an insight that this was probably how Bullfighting started... some kid daring another kid to go stab a bull, and him doing it for attention from girls. And that sport is still heavily associated with machismo. One other thing on the macho side - like, my mom roller skated when she was young, and even she got a pair of roller blades. You can't really be dangerously cool doing something your mom does.