This has to be one of the most difficult financial situations through which to navigate. Important relationships are at stake and it seems to me that the most socially acceptable (and easiest) thing to do is to give if you have it. Money problems are one of our last cultural taboos and so anyone revealing theirs is already feeling vulnerable but it is very difficult to consider giving or lending money without wondering how they got into the bind in the first place.

About a year ago, an email request came from a member of our social group soliciting donations for another member of the group, I’ll call Sue, whose business had failed and who needed money for a certification program which would hopefully launch a new career. It sounded like a good cause and we were doing okay so we sent her a check for $100 which she did in fact use for that purpose and for which she was very appreciative. In a subsequent conversation with Sue she explained how she was very frugal and though she shops at Ann Taylor for her clothes, she was considering holding off on the purchase of a new car since her current 5 year old model wasn’t yet giving her any problems. Now I’m really working on my nonjudgement but considering that I shop at Goodwill and other second hand stores (with the occasional splurge at TJMaxx) and my well maintained 11 year old car suits me just fine, I’m no longer certain that the donation went to a good cause.

My mother, who’s never met a dollar she couldn’t spend (plus interest), occasionally hints that she needs a new couch or a new mattress. She has sufficient income, multiple vices and has spent beyond her means her entire adult life. She has often said how she feels that people with money should be generous and she knows that I have money saved. What she doesn’t know, and will never understand, is that if I spent money that way she did, I wouldn’t have any either. I just end up looking like the selfish daughter who won’t help her poor mother!

We’ve been invited to a party this month at a local club that will double as a fundraiser for another member of our social group. From the outside, her life looks quite comfortable. She lives alone in a much bigger home than I share with my wife. But in reality, I have no idea what kind of challenges she faces. Perhaps she has a medical crisis. Perhaps she has lost her job and had no emergency savings of any kind. We may never know. We’ll probably go to the party and we’ll no doubt give the requested donation. But will it really help? In the long run? Wouldn’t a gift of financial coaching, while socially unacceptable, be more useful?

I’d really love to hear how others handle these delicate situations without feeling like either a louse or a fool.

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