My brother has stolen small amounts of money from me before to pay for drugs. (He owes me somewhere in the realm of 50$, but I stole some pot from him which he never found out about, so now it's more like 20$) He keeps promising to pay me back, but he still does not have a job and is not actively looking for one, because he is content to be mooching off my parents (who are tired of listening to his excuses). He recently one 100$ in a fantasy football pool, but instead of paying people back (he's also had some run-ins with dealers and apparently owes more than just our family), he goes and buys a half ounce of mexican crapweed.
In terms of lending people money, I don't have a lot to lend, but I don't lend unless I'm absolutely positive I'll get it back. Or unless I believe it's something I'm willing to lose money on (an investment, in this case). I lent my best friend 200 for car insurance, which I got back, and I've been buying computer parts for a friend of mine so he can start writing (which he's really good at, he just needs a spell checker/grammar checker) which he can't afford because him, his girlfriend, his brother and a friend/tenant are basically paying rent/utilities on the house while their mom lies on the couch watching movies/tv all day. Two of those people are currently out of a job, and one's a drug dealer, and they've got hospital bills to pay. Basically I'm helping them because they're up shit creek and don't deserve it.