This is a great topic. I have definitely been upset when I've helped someone out and then they've spent money on what looks to me like frivolous stuff. My husband is overly generous and in our early years he would always want to pick up the tab for people who I knew damned well had much more money than I did. But also, I'm very budget-conscious/cheap and have sometimes thought that has led to others thinking they should offer to treat me. I don't want to be treated! I want to either do something cheap/free or just hang out. If we do go do something, I want to pay my share.

Many years ago, I had a home business renting/selling breast pumps and other equipment to nursing moms. I would rent the hospital-quality equipment for free to a mom in need. One mom, whose baby was in the NICU, asked for me to give it to her for free, because while she did have money, it was set aside for buying a house. Our living conditions -- which she knew! She came to my house to get the pump! -- could best be described as humble. I still marvel at the fucking nerve of someone who was pretty well off asking somebody who was OBVIOUSLY low-income to subsidize her. Moms who were in a tight place were different -- I was always willing to rent them the pump for free.