How do you deal with a friend who owes you money?

Nobody likes being around a person who thinks that they have free rein on your wallet, but there are plenty of individuals out there who will act like that with you if you aren’t careful. Whether you encounter a professional freeloader or the kind of person who is simply too good at ignoring when others go to significant expense, they are likely to cause conflict at some point.

The most important thing when dealing with this type is enforcing and sticking to some firm boundaries. Sadly, it is a lesson that many are only going to learn from experience. It is often the case of getting burned once and learning not to get burned again. It isn’t nice to lose money to someone you eventually feel does not deserve it, and there is every chance this investment will not be a one-time thing. It can ruin events and things you looked forward to, purely because they are not interested in changing their behavior. Dealing with this does not come easily to a lot of people, but it is a skill worth developing sooner rather than later.