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My sister and I were talking earlier and she mentioned a silly recurring mistake her boyfriend makes. They're both in their early twenties for context. When he cleans, he throws out opaque bags (like the kind from a grocery store or paper bags) without checking what's in them. He has done this twice, later repaying the owners for their contents, but with moderately-priced items for college students. She formally laid out a rule that he has to check before tossing stuff in bags when they're both cleaning, and treats it like "oh, he's just like that." I reminded her that this is not a normal behavior, since grocery bags could have virtually anything in them, and she realized that she has never done this before in her own lifetime either.
This is to say that it's easy to accept that what's happening is normal for a person if they say as much. Don't forget critical thinking for yourselves and don't be afraid to point out that something is, in fact, egregiously stupid.
Does he "accidentally" throw away his own stuff? That's the mark.
He knows what he's doing. Learned helplessness is his game.
Shut it down asap or succumb to it
This reminds me of something I did once when I was young and stupid -
It was my first week of doing low-level admin work at a school. I was tasked to setting up a room for the next class. The kids left a bunch of their stuff and a bunch of messes in the room - so I just sweep all their stuff straight into the trash.
This wasn't a well thought-out ploy or anything. I was frustrated because I didn't think "maid" was part of my job description. So that was my way of lashing out.
Anyway, my boss came in to redo it, without throwing people's stuff out. I was miraculously not fired. I felt bad she had to redo my work, so I did the work properly every time after that.
This might not work on a guy, because they might not have the capacity to feel shame. 😆