Should Sister Lend to Her Deadbeat Brother?

Peter and Molly,

My brother lost his job about two years ago. He moved back into our parents' house, but wouldn't look for more work, and he eventually wore out his welcome. I'm not sure how he's making ends meet, but he has an apartment that he shares with some friends. He complains relentlessly, about how unfair the world has been to him, and how unkind our parents were. He has tried college, but quit, and had quit several other jobs before being laid off. He has never shown any ambition that has lasted more than a couple of weeks. He called me last week and said that he has found a cosmetology school that he'd like to go to, and that he could finish in a year, but would need $2000 tuition, he asked me if I could help out. I want to be charitable and non judgmental and he could really use the help, but this is also his hole to dig out of, and while I have the money, I don't want to throw it down a drain. What is your advice?

Stressed Out Sibling

Stressed, it sounds to me like your biggest concern is about whether or not your brother is actually going to stick with cosmetology and be able to make a career out of it. What you could do is offer him the tuition, but only if he finishes the program, and expect him to pay it back if he does not finish the program. Not only does that protect you, but it might give him the incentive he needs to stick things through.

It is a universal truth: Never lend money to someone you love that you ever want back. If you want to give the money to your brother, you can never ask for it again. So should you give it? In my mind it is an equation, is that much money worth to you the chance that you think your brother will finish the program. I don't know what your financial situation, and you're kind of vague, if you can afford the chance it works out than go for it, otherwise give him the number to a college loan office.

You know Peter, I'm a little surprised that you would be the one that tried to distill a human relationship to simple equation. There are a lot more factors in play here. Stressed's brother needs help, badly, he is out of work for years, and trying to get by on his last strings. So who should he turn to for help? The government, the church? Maybe eventually, but first he should turn to his family. That's what he's done, and Stressed should see her role in that. That doesn't mean she needs to be taken advantage of, but it does mean that she should focus on helping.

Then I guess the equation is (Chance he finishes + Charity constant)/Money sacrifice. Honestly I agree with Molly that you should help if you can, but you need to be very honest about the "if you can" part. 

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