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I am currently trying to figure out if he really is that daft or if it is intentional.
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It can be both. I've known a few people who were often doing stupid stuff, getting in trouble, and getting someone else to pay the bills. Why bother to be smart when someone else will fix your problems for you?
Most bank accounts will let you set up regular, automatic transfers to another account. Maybe you could try doing that with your H? so you don't have to ask him for money or remind him all the time.