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Dear Jeanne and Leonard: When “David” and I got married, we agreed – formally, in a prenuptial agreement – to keep our money separate so that each of us can leave what we have to our children from our first marriages. Unfortunately, David’s only child, “John,” who’s a lawyer, never manages to live on his income, which means David always has to bail him out. While that’s discouraging enough, now David is seriously considering giving his son a large, six-figure loan so John can quit his job and start his own law firm. When I pointed out that someone unable to manage a household budget is a poor candidate to run a business, David got angry. He said that he’s free to do what he wants with his money and that he’s not asking for any of mine. He also said that if John fails to repay him, it won’t make any difference – that the loan will just end up being an advance on John’s inheritance. But it will make a difference: If David isn’t repaid, I’ll have to support him when he retires, and that means I won’t have much left to leave to my own children. Am I wrong to insist that David listen to reason?

– Susan, Northern California

Dear Susan: If insisting will make a difference, by all means do so: Do everything in your power to prevent your husband from indulging his improvident son at the expense of your kids.

We hope you succeed. Because if David refuses to understand that a substantial depletion of his nest egg would necessarily result in a depletion of yours as well – if he refuses to listen to reason – you’re basically left with two choices, neither of them attractive. One is to give up and hope that John succeeds in spite of himself. And the other is to consider ending your marriage before your foolish husband and feckless stepson seriously erode the estate you plan to leave to your children.

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Dear Jeanne and Leonard: In the past few months I’ve received two letters – one from a friend I rarely see, and one from a business associate with whom I’ve never been close – each one asking for money. Specifically, they each asked for contributions to the charitable organizations that are sponsoring their trips to the Third World, where they’ve volunteered to work with the poor. I don’t doubt that these efforts are worthwhile. But my wife and I contribute both time and money to a variety of equally worthwhile causes, and it’s never entered our minds to ask others to contribute to the organizations we support. So am I overreacting to be put off by letters from people I’m not close to asking for money to send them to Guatemala, in one case, and Africa, in the other? Or is this the new normal?

– T.R., Lake Oswego, Ore.

Dear T.R.: You’re not wrong to be put off, not in our book.

Once upon a time, you were expected to buy Girl Scout cookies from your neighbors’ daughter, but that was about it. Today there are charities that build multimillion-dollar fundraising campaigns around the willingness of their supporters to hit up everyone they know for money. While most of these campaigns involve the supporters asking friends to sponsor them on a walk or a bike ride and not a trip to the Third World, they’re all predicated on the conviction of the folks’ soliciting donations that there’s something uniquely worthy about the charity they’re supporting – something so worthy it merits putting their friends and acquaintances on the spot.

Like you, we have our own favorite charities, and we wouldn’t dream of pressing others to support them. But it feels as if, on this front, we’re in a losing battle.

Please email your questions about money and relationships to Questions@MoneyManners.net.