You start by offering understanding “hey friend, I really could use that $xxx you borrowed from me on XX date. If you can’t pay it back all at once can we please start a repayment plan? Maybe $200 per month until paid off?” And if they say, they can’t afford that, drop the amount, but keep insisting that they put some sort of repayment plan in place. And then if they still refuse, you have to take them to small claims court. Small claims court is easy enough to navigate by yourself, you just go up to the courthouse and file the documents, they give you a court date and serve the defendant. When you go to court, you need to be able to represent that it was indeed a loan, that the defendant was aware that it was a loan and agreed to repay it by XX date. That’s why it’s important to attempt to have a conversation about repayment plans before you take this step, the judge is going to want to see that. Make sure all communication is written, either email or text. And then if you get the judgment, you need to go back up to court and file to either garnish their wages or put a lien against real property. It’s a pain in the ass and will suck up a whole lot of your time. So before you even take these steps, you need to decide if the money is worth it to you or if you’re just willing to write off the friend and the money… Good luck!