I have no quarrels with people who don't like super-hard difficulties, but I enjoy them under certain circumstances. The Uncharted franchise is a good example here -- on Crushing, they're challenging throughout and a little cheap in spots, but they're fine overall, and I like having beaten the game on a difficulty that the game isn't really designed around. By way of contrast, The Evil Within is quite difficult in spots on normal. I have absolutely no interest in playing it on everything-one-hit-kills-you mode (that's literally exactly what it is, by deliberate design).
One of my favorite video gaming experiences was beating Dead Space 2 on hardcore mode -- hard-to-very-hard difficulty and you're only allowed to save three times. That was a great, tense as hell experience. Perfect for that kind of game.
None of the Souls games are as hard as people sometimes make them out to be, but I love the lack of hand-holding and the complete not-giving-a-#### if you can't get past some particular boss. It's as if the game is telling you "Sorry, but if you want to see the rest of this game, you need to get good first." I really love that as an old school throwback. I've already platinumed this one, but I'm still working my way through the game again with a character built around the Blade of Mercy, which is sort of like activating hard mode when you're used to a weapon with reach and the ability to stagger enemies. This change of pace makes the game fresh again.
I have a mild OCD streak and I have no problem beating my head against the wall for a bit if it's a game I enjoy. But it really depends on the game.