A: Asking for your money back is not a wrong thing to do. If you gave and he took the money as a loan, then he must return it by a stipulated date or face consequences for not returning it. I hope you have some circumstantial proof in terms of messages or emails that you lent him the money. Do not fall for the guilt game he is trying to play with you. It is your hard earned money and it makes no sense to feel guilty about fighting for something that is legitimately yours. I would also say, depending upon the amount you have given to him of course, I would completely forget about it if it is a small amount and ensure my mental peace and cut my losses. Related reading: Money, marriage and managing differences However, if the amount is big enough for you, I would urge you to feel no tinge of guilt at all in trying to recover it. Ultimately the emotional question is, “Is it worth my time and energy to pursue this guy for the amount I have lent him?” Best Deepak Kashyap