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He is very private, and will not share any health-financial information with me. I've tried the being nice method, no success. Then I attempted the direct to the point way, and he just clammed up after that.
Recently he has approached me asking for money for daily living. I gave him some but now I worry that this will start a procession of asking for money all the time, I don't mind helping him, but not knowing what his financial standing for now and the future is driving me crazy.
Has anyone else dealt with a situation like this ?

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If somebody - anybody - asks you to give or lend him money, that entitles you to ask reasonable, relevant questions in a courteous way. If you do that and the questions remain unanswered or the person takes offence, no deal.

This is the second new topic within a week featuring a parent asking a geographically distant child for money but refusing to share basic information. By the way.
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vonrock Mar 2019
If a you have the money to lend a friend or family member,
lend it, and never ask about it.
That’s a true friend.
our reason assuming, theirs trust and hope.
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It's difficult to know what's going on with a senior when they live far away. Even with phone calls, emails, it's hard to know for sure. I might plan a trip to stay in the house with him for a couple of days so you can really see how he's doing and what's going on. It could be he's not managing his fiances well or someone is misusing his money. He may not want to let you know, because, he's embarrassed.
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If he's lost the ability to reason, there may not be anyway to convince him or get him on board with sharing or asking for help. Sometimes, the worst happens and the bills unpaid, power cuts off, etc. When, I got to my cousin's house there was unopened mail on the table, unpaid bills, power close to being shut off. She told me to PLEASE help take care of that mess. but, previously, she was secretive and not open to help. I think she finally got scared.

My preference is to be straight about it and just explain in a calm and caring way that all seniors need backup plans in case they get sick and need help AND that, it worries you that he seems to be struggling financially and ask why. The way he handles it, might provide you with some clues.

You might also get a legal consult with an Elder Law attorney in the jurisdiction where he lives, to see if they have any suggestions.

You might go online to see if he has any unpaid property tax bills. Sometimes, they go unpaid if the senior is not able to manage all the bills.
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I was a distance caregiver but not at that distance. Mother appointed me POA -financial and health, finally, after her financial adviser pressured her to. For years she wouldn't do it. Problems with finances can be one of the first signs of dementia. Is there any family close who could visit him and let you know how he is managing? Are you the only offspring?

I think your concern is valid. I would not give him any more money without full disclosure of his health and financial status, and in fact him signing a POA financial and health. If you are the one who will be helping him as he ages, that you need those documents.

Are you able to visit him and make an assessment for yourself? Is he managing housekeeping and meals? Are his bills paid? Does he gamble or drink? Does he take care of his health? Does he have any social life? Does he have a trusted friend/pastor/lawyer you could contact and who would help your father understand he needs these documents?

If he has dementia or any progressive disease, like heart disease, he will need more and more care. More specific information about his health/situation would be helpful for responders. Good luck!
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If he never asked before, find out why he is asking now. He might have 'credit card fraud' that is bankrupting him. He could be a victim of a scam - so many are perpetrated against seniors.

If he's been donating to charities, he needs to stop.

If there is a genuine need for assistance, then help him to find it. He might be eligible for Medicaid and 'food stamps' as well as cash.

Take every step you can before you send money - once you start, you are taking on a responsibility that will be difficult to stop.
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You can call his local Adult Protective Service and ask for a "well visit". Call his PCP and explain that you know they can give you no info but that you are worried about Dad.

I, too, would give him no more money telling him you need to see his finances.
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You have a right to know why he is asking. Do you know if he might have a "girlfriend " or someone else who he is giving some of his money too. You have the right to ask him why is he suddenly needing money?
Being suspicious if that is what your gut instinct is, is ok. Often times elders are preyed upon or they send their money to schemes etc. so it’s best to ask.
do you or anyone in the family have a POA in place in case you need to handle finances? Does he have any signs of dementia?
if you feel like you absolutely are bound to send money you could send a gift card to a local grocery store. That way you know where the money goes.
i say this because my husband's half sister who he didn’t grow up with asked him for money as they were behind on house payments and would lose their home. He gave them several thousand. Guess what happened? They squandered it and lost their home. In hindsight he wishes he’d made the checks out to the mortgage bank.
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I should add that when I started reviewing my LO's finances, after her dementia set in, I discovered that she has overpaid some things that were unnecessary. She had sent magazine companies so many renewal fees to the point that they could no longer accept them. She forgot she had renewed the subscription several times. Plus, repeated donations to SPCA, Fireman's fund, etc. She wasn't in a position to be doing that. It could have gotten a lot worse.
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When my father was having difficulties with money but still legally competent, I paid his bills but didn't give him money directly. I enabled him to blow his money by spending my money on his utilities and supplemental health insurance but at least I knew the lights were on and when he needed to go to the doctor or hospital the insurance covered most of it.
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You really should pay him a visit to get a realistic view of whats going on with him physically, his living situation and the state of his finances. You need to make sure he is not being financially exploited or has not already been victimized by scammers.
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