My Dad is very emotionally stunted and never really grew up. He would constantly go around to his parents and ask them for money, ask them to buy him a car, a computer, etc. He would 'borrow' our birthday money when we were little and we would sometimes never get it back. My grandparents opened a savings account for me when I was born and he withdrew all the money from it and spent it when I was a baby. He has been unemployed for years, living off my DM and his parents. As soon as I got my first job at 16 he started asking to borrow money from me. 'Borrow' is a loose term because how can someone unemployed pay you back. He withdrew and spent all his pension money (from the few years he did work when he was in his 20s and 30s) and just wasted it all on a motorbike and other rubbish.
He can't comprehend that being unemployed means he can't just get what he wants. Any time he would do me a favour he would hint/joke about wanting to be paid for it, like dropping me off at my university halls when I was a student, or helping me put together furniture. It makes me cringe and feel so uncomfortable and I don't know why.
It doesn't just extend to money. Growing up I have had to hear all about his loneliness, his marriage issues with my Mum, his depression, his affair and that carries on now. I tell him that I don't want to hear it, but he ignores me and says he has no one else to talk to.