A certain person owes me a lot of money, for a long time already. They said that they would pay me back, but keep pushing it off and have even lied to me. I haven’t talked to anyone about it because I didn’t want to speak lashon hara, but I think I might explode if I don’t tell someone soon. I don’t want to do anything that might ruin our relationship, but I do need the money. So my questions are: Am I allowed to tell a friend about this- if so what, and to what degree? Do you have any suggestions what I can do to actually get the money back without damaging the relationship?

Telling a friend would be lashon hara unless you know the friend would be able to use his influence to get the money back. Suggest to the borrower that you go to a din torah or, if you prefer not to do this as yet, persistent, unflagging reminders are often sufficient. Your friendship with your borrowing friend will likely get stronger once he stops feeling guilty about not paying you back.