My theory is he hates being alone, and desperately needs to have people around him. Which is fine, some people are extroverted, but to me its exhausting to deal with. I am an introvert, and can only take so much human interaction before my brain fries. In this case, this guy is creating a hanging out schedule that is becoming excessive to say the least. For example, yesterday i met up with him at 5, and didnt get home until past 10. I was gonna cut it short, but then he decided to put on a really long movie at 8 PM. I don't mind movies, but i absolutely despise 2.5 hour long movies. And at this point, it's starting to get a tad bit ridiculous. My second problem is the idea that only he has ever suffered hardship. Sure, you live a relatively hard life right now, and yes, i am trying to help you. However, I have also had to deal with hardship in my life. I just don't gloat or brag about it. He acts as if he's the only guy who'se ever had debt, or had to make a difficult decision. Overall he's a great guy, fun to talk to and stuff, but I cant quite understand the sheer dependence on others. The guy is definitely in his late 70s or so, not exactly sure what the exact number is though edit: a good example, i told him i was busy today and cant help him. My statement didnt even register to him as a problem or a possible issue. He just expects me to drop everything and go help him, regardless of what else is going on in my life