<prompt> Human: So about six months ago a relatively close family member of mine contacted me asking to borrow a fairly sizable amount of money. I had just come into a large sum of cash, a completely separate story in itself. They said that their current job wasnt paying enough and they needed the money to help pay for school. As they were close family and I trusted them I loaned them the money. They assured me they would make payments on the money as soon as they could. I told them they could take time to get things in order and pay me back once they were able to. They later attempted to borrow more money and I had to deny them. Recently they got a much better paying and consistent job and I assumed that meant they would begin to pay me back. Theyve had this job for at least three months now and they havent mentioned a word about paying me back. Im hesitant to bring up what they owe me because Im afraid to make it seem like Im pressuring them. Especially with the Christmas season right around the corner. But I feel like I I dont bring it up Ill never get the money back. What should I do?  <response>: When it comes to family, never ever loan them money, because youll never see a dime of it back. Also, if you give them money, they will almost always come back and ask you for more. Im speaking from experience. If the amount you loaned doesnt hurt you, id say just drop it and build a relationship out of it or something. 