I’ve known my best friend from college for several years now and I’ve never felt luckier. He always tries to make time to talk (despite living very far away), he’s helped me through some personal stuff and given great advice in the past. If he has one flaw, it’s that he asks to borrow money every so often. This only started after he moved away and at that point, I had already known him for a while. Now, luckily, he’s always been able to pay me back fully, even though it can take a while (couple months at most), and I’ve said no a few times in the past and it didn’t seem to bother him at all. But I’m a little concerned given the large amount of money he asks for each and I’m wondering if he’s in some kind of trouble. Should I approach him about this?