I’ve lived with an elderly friend for 16 years and he made me his executor — I’m not a gold digger, but now I suspect he’s broke

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I’ve lived with an elderly friend for 16 years and he made me his executor — I’m not a gold digger, but now I suspect he’s broke
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An old friend gave me a place to stay when I needed it most, and now I'm the executor of his estate. I'm helping him financially and can't plan for the future. Dear Moneyist, what do I do?

I am unsure how to word this without sounding horrible but, this is so unique, I fear that you won’t want to advise because so much detail is needed. But here goes nothing:

So here’s the issue: He retired due to chronic obstructive pulmonary disease, and he is in remission from cancer. I have given a lot of resources to helping out with rides, meals, company and more. I have power of attorney. I am named as sole executor and beneficiary in his will, completely ignoring all the people he has known far longer.

He is still very sharp, but doesn’t seem to understand what we’ve sacrificed, most of this being without any specifics other than vague allusions to his wealth over the years. This is such a hard thing to bring up with a non-family member without seeming improperly interested. I’m also so awkward on top of that. Getting the papers done before he had surgery was hard enough.

Try the “open the wallet” strategy. It’s the conversational equivalent of those tea lights sitting on a table inside the entrance of Ikea. The store eases you into buying with something small. You hardly feel a thing. How about: “I’d like to make plans for the future. Combining households could be helpful for all of us, if you are still interested, but my partner and I would like to figure out all our finances in order to do that.” You’re being clear and honest about your intentions.

You can tell yourself that there was a bond or some kind of magical friendship born out of that first meeting, but the truth is that this was a transactional relationship from the start. As well as being honest with your friend, you should be honest with yourself. Your friend was lonely, and you needed somewhere to live.

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