Home Question Box Question Box Flash I gave my sister $500 to pay bills. She bought shoes – nice ones. Should I demand repayment now? By Neela Kale September 21, 2012 Lending money to family members can be very tricky. It may help to remember that money comes and goes, but she will always be your sister. Even if you don’t have the greatest relationship, or if she doesn’t always make the best choices, sisterhood is something that money can’t buy. Rather than demanding anything, talk frankly with your sister. Give her the benefit of the doubt — say that you know things have been tight, but you noticed her cute shoes and wondered if the sale was still on. (A sense of humor always helps.) Then remind her that you’re expecting her to pay you back at the time you agreed upon. You may think twice if she asks to borrow money again in the future. Alternately, if you’re really concerned about her ability to manage her finances but do want to help, you could offer to assist in a specific way — by taking her grocery shopping or paying a bill directly, for example — instead of by cutting a check.