Kinda sounds like you have maybe enabled his dependent behavior. Sometimes the best thing you can do for someone is to let them suffer the consequences of their actions. He also is not being very fair at all to blame you for worrying about your money in this time, especially considering what he did with the money you gave him. I would definitely start thinking about all the times he has been there for you. He may be a taker with money but a giver in other ways, but you need to make sure he isn't a taker in all ways, including emotional support, sex life, etc. But really i think you should be more careful about lending money. I totally respect that you don't mind helping people out monetarily, but there is a big difference between helping someone out who needs it vs enabling poor decisions