Dear Blake,

When my boyfriend found out I have the money to do it, he asked me to pay off his car. Now, because I said no, he won’t answer the phone or talk to me. I have helped him in the past, but he continues to ask me for money. I think he’s using me. He tries to make me feel guilty by accusing me of not caring about him because, “If I did, I would pay off his car.”

I’m 58 years old, and the money I have is for me to live comfortably, not to spend on him. I told him as much, and he still insists I should help him with his bills. We live separately, and I suspect he’s really just interested in the money, but I’m afraid of being lonely. What should I do?

Signed, Evelyn
From Chicago, Illinois

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Dear Evelyn,

Your boyfriend appears to be selfish and emotionally manipulative. So, based on that, I think you should put him in a position where he feels bringing up the subject of cash around you, is a waist of time (and money). Here are some other ideas. Tell him you have developed a gambling habit, you’re broke, and you insist that he sells his car to pay for your trips to Las Vegas. Or, don’t call him anymore, and when calls you, tell him you have changed your dating standard, and you only get involved with men that are debt free, plus they have to have a fat bank account… when they give you their ATM card. Or how about this one. Tell him all the money you “had” was seized by the IRS, and you will remain penniless during your upcoming trial in federal court. That information alone will probably inspire him to end the relationship. Finally, if you really want to help him, then loan him the money. But to make sure he doesn’t ever miss a payment, tell him that the only thing you will accept as collateral is one of his kidneys. And if he has a low credit score, request one of his lungs too. I hope this helps.