Fighting an 8-headed snake-woman thing, I blow all my SP on my most powerful attack, only for her dodge every hit of it due to having 8 heads(no idea how that works). Never fully recovered from that, and spent the rest of my life(which was not a quick kill) as her toy.
Monster Girl Quest again. Yamata no Orochi is not easy, but I've learned that, so far, you can bypass the Colliseum, even though there's no reason to. Luka probably needed those levels from it.
An Otaku girl sneaks into the edge of a city, and after multiple failed attempts to give a previous character a proper cremation(goddamn it, burn already), I decide to fortify a nearby house. All the windows are surrounded by pits, almost all are spiked, and the house is well stocked. I go to sleep, and the next morning there's a coyote outside. I kill it, then leave the house to butcher it, only for a wolf spider to get massive numbers of headshots in a row, plus poisoning, while I can't even hit the damn thing with a crowbar.
Cataclysm DDA. She's not actually dead yet, but she won't survive even if she does kill the spider.
And I can't believe I never figured out that I can disassemble the 3ft strings you get from smashing windows until now. I needed those 6in strings.