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Should I Date a Man Who’ll Leave Me Broke When He Dies?


Dear Penny,
Recently I met a man I liked. Unfortunately, he’s divorced with five kids. His kids live in a different state far away.

On our first date, he made it clear that he is very wealthy and that when he dies, all his money is going to his children. I immediately got turned off. It just didn’t sound right. He broke the family unit that included five children, invited someone new in (me), and said, when I die, you’ll have to get a blanket and sleep outside, basically. I feel that’s wrong.

If he wanted all of his money to go to his children, he should have stayed with his ex-wife. That way both parents are in agreement where the money goes. He’s unwilling to go back because she cheated, and she’s on drugs. So his headache has become mine.

He’s not the first guy I’ve heard say this, and I think it’s awfully self-centered, especially if we are together for a lengthy amount of time and I contribute to the marriage or relationship. I’m just scared that we might be together for years, he passes, and the kids try to sweep everything from underneath my feet, which I would never allow. I’m not going to be pushed onto the streets with nothing.

There needs to be equality. If equality cannot be created, he should stay single. I don’t have kids, and I’m usually opposed to dating people who do. This is one of the reasons.

A partial reason for getting married is to build wealth together. If we were married for a long time, I would make sure money is entrusted to him, as well as a few close friends and possibly my nephews. I would never tell him he’d get nothing.

This just isn’t my Prince Charming. It’s not what I wanted for my life. I don’t think that he understands that if we are together for a lengthy amount of time, that his kids would be my kids anyway. They would want for nothing. I like this guy, but I feel his views for my future are not right.

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I guess he picked up on my frustration, and he’s not texting much any longer. I did not discuss this with him, but I think he gets the drift. Any advice?

P.S. He may be bringing the kids to live with him because of his ex-wife’s newfound drug issue. The two oldest don’t want to live with him. He said he’s not dividing them. Either they all come, or they all stay.

-Unsure in Pennsylvania

Dear Unsure,

Did he really say, “When I die, you’ll have to get a blanket and sleep outside”? If these were his words, I wish you’d ended the date right then. But I have a hunch this is your interpretation of what he told you.

Estate planning is a poor conversation topic for a first date. Before you worry about how a potential partner will care for you in death, think about what actually living with them would be like.

This man gave you valuable insight into how he treats the people in his life. To be clear, I’m referring to his kids, not you. It seems pretty clear that he never invited you into the family unit, nor did he make his headache into yours.


I’m skeptical of people who make a big show of wealth or disclose deeply personal details about their ex on a first date. But even if you take what he told you as truth, he has the means to live wherever he wants. Yet he chose to move out of state, leaving his five children with their mother who misuses drugs. Would you feel better about dating this man if he told you his kids get nothing when he dies?

If you want to be someone’s No. 1 financial priority and build an empire together, I suppose dating someone with no kids makes sense. But keep in mind that the older you get, you’ll be screening out a lot of potential mates.

If you’re worried about being left broke in old age, quit waiting for Prince Charming. Be your own Prince(ss) Charming. Focus on your career, your retirement savings and living within your means.

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You may think that this man and others who think like he does should stay single. But you don’t get a deciding vote on who throws themselves into the dating pool. What you can do is set standards for yourself and who you pursue a relationship with.

Focus on finding a decent person before you get into the nitty-gritty of each other’s finances. No two people see eye-to-eye on everything. But reasonable people can compromise when they’re building a life together.

Hopefully, you can apply what I’ve told you to future suitors. But you really don’t need advice for dealing with this man. You’ve decided your views are incompatible, and he’s barely texting you. Consider this a problem that’s solved itself.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected] or chat with her in The Penny Hoarder Community.


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