Should I help my boyfriend get out of debt?
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Honest relationship or not, I would say "no". You are in your 50′s and you both need to reckon about your financial security. Even with a repayment plot, things could go south. Loaning money is never a excellent thing, even to family, close friends. If you were married and equally sharing assets, I may reckon differently…
If you want to help him, the best thing to do is sit down with a financial advisor and help keep him on a budget and possibly negotiate down some of his debt. He’s a developed man who got himself into the situation, and after only knowing you for such a small time, has no place to question you for that sort of money.
Reckon about it, your kids are growing up and will be in college or starting families soon. It makes more sense for you to place that extra money you have into an interest bearing account and profit from it rather than give it away and earn modest or no interest from it. Right now you need to concentrate on providing for yourself for retirement and for the future of your family, not this man.