Should I date a man who’ll leave me broke when he dies?

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    Dear Penny,

    I recently met a man I liked. Unfortunately, he is divorced with five children. His children live far away in another state.

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

    If he wanted all his money to flow to his children, he should have stayed with his ex-wife. So both parents agree on where the money goes. He’s not ready to go back because she cheated and she is using drugs. So his headache has become mine.

    He’s not the first person I’ve heard this say, and I think it’s terribly self-centered, especially when we’ve been together for long periods of time and I’m contributing to the marriage or relationship. I’m just afraid that we could be together for years, he leaves and the kids try to sweep everything from under my feet that I would never allow. I am not pushed onto the streets with anything.

    Equality is a must. If equality cannot be established, he should remain single. I don’t have children, and I’m usually against people who have them. This is one of the reasons.

    Part of the reason for getting married is to build up wealth together. If we were married long, I would see that money was entrusted to him, as well as a few close friends and possibly my nephews. I would never tell him that he is not getting anything.

    This is just not my Prince Charming. It’s not what I wanted in my life. I don’t think he understands that his children would be my children anyway if we were together for long periods of time. They would want for nothing. I like this guy, but I think his views about my future are incorrect.

    I guess he noticed my frustration and doesn’t write much anymore. I haven’t discussed this with him, but I think he understands. Any advice?

    PS Maybe he’s bringing the kids to him because of his ex-wife’s newly discovered drug problem. The two elders do not want to live with him. He said he didn’t share it. They either all come or they all stay.

    – Unsure in Pennsylvania

    Dear unsure,

    Did he really say, “When I die, you have to get a blanket and sleep outside”? If these were his words, I wish you had ended the date right away. But I have a hunch, that’s your take on what he told you.

    Estate planning is a bad topic of conversation for a first date. Before you worry about how a potential partner will look after you in death, think about what it really would be like to live with them.

    This man has given you valuable insights into his dealings with the people in his life. To be clear, I’m referring to his children, not you. It seems pretty clear that he never invited you to the family unit, nor did he make his headache yours.


    I am skeptical of people who put on a big show of wealth on a first date or reveal very personal details about their ex. But even if you believe what he has told you to be true, he has the means to live wherever he will. Still, he decided to move out of the state and leave his five children with their drug-abusing mother. Would you feel better about dating this man, if he told you that if he dies his children will get nothing?

    If you want to be someone’s number 1 financial priority and build an empire together, it makes sense to date someone without kids. But remember that as you get older, you will weed out many potential partners.

    If you worry about staying broke in old age, stop waiting for Prince Charming. Be your own prince (s) charming. Focus on your career, your retirement savings and your life as much as you can.

    You may think this man and others who think like him should stay single. But you don’t get anyone who plunges into the dating pool. What you can do is set standards for yourself and the people you relate with.

    Before dealing with each other’s finances, focus on finding a decent person. No two people see everything at eye level. But sensible people can compromise when building a life together.

    Hopefully you can apply what I have told you to future applicants. But you really don’t need advice on how to deal with this man. You have decided your views are incompatible and he hardly text you. Think of this as a problem that has resolved itself.

    Robin Hartill is a certified financial planner and 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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