I have had a variety of disappointing conversations with folks over the last 3 years. First was how my DHs family could not understand how it was that he quit his job when other family members cannot find a job. It was very uncomfortable. I finally sat his dad down and for the first time in 24 years I opened mint and let him look at our finances. He perused them then told my husband, "keep this woman!"
Later I tried to imbue the sense of frugality to my mother. OMG what a horrible conversation that was, I just plain gave up.
Just reunited with a long lost friend, after about 12 years. I did warm him up to my financial strategies, his family is even worse than my family. That went ok but I was so disheartened that his income will make any FI planning nearly impossible. He really needs to 1. find a roommate living situation, but wont, and 2. work at changing his career, or take a leadership role after 17 years in his field ($16/hour).
I never, ever talk about anything financial at work. I did have to tell my boss about our first duplex (cant remember the exact circumstances now), he saw the picture and asked, so are you buying the whole building or just one half? When I said the entire building his face was like....wow... He is out of state and where he lives a duplex would be very expensive. I've kept quiet since then. Also at work I never pay for lunch and sometimes that causes a stir since I don't ever want to run out and get Teriyaki, Thai or a burger...ever. I just thank them and say I brought my lunch.
I really, really want to go over my sister in law's financials, they are in some dire straights, but I don't know how to approach her on it. She knows her brother is "retired" because we want it that way (I would not say we planned it, but when we looked at our numbers it made sense for us). We drive used cars, own property, live in an older home and are not keeping up with any Joneses. We have remodeled this old home ourselves and its nice, but not fancy or large or anything. She always looks stressed and unhappy and I know that they are not good at finances. But what can you do?
I would say work on your probing strategy and be excited when you find a kindred spirit:)