Basically any non-fight encounter/interaction in a dungeon. Similar wording for what is used in Darkest Dungeon.
Also for your first question, i think its mostly up to rng from multiple different aspects as you play through the game. You can kinda force certain desire stats through cursed items, certain classes, and maybe a few other ways but im not 100% sure on that.
To add on with a different point from CloudJiv. You can test "?" items on people you're not dedicated towards leveling up. So if you have class specific items that might be cursed you can wait until you have a back up person to test whether it is cursed or not, otherwise just pull a random new recruit that you're not interested in leveling and test all potentially cursed items on them. Then you can dismiss them if they're stuck with annoying cursed items or keep them to try and unlock the fun/good cursed items for future use.
That being said i definitely felt that way early on in my first attempt too.
