The Problem: Dad is becoming a road hazard.
The Plan: Get him to turn in his keys—voluntarily—by enlisting the help of a trusted, objective third party, like the internist he's been seeing for decades.
The Talk: Start by saying "A friend's father just totaled his car, and when he went to the hospital, the doctor did some tests and said he absolutely shouldn't be driving because of his vision." Says Abramson, "It might just strike a chord. Then bring in the family doctor."
The Problem: Mom, a widow, can't handle the responsibilities of living alone in the house she and your father once shared.
The Plan: Find out what is most likely to positively influence her impression of a retirement residence. Water aerobics? A weekly mah-jongg game? Meals brought to her private garden? It's all out there, says Abramson. "Find the right place with the right perks before you think about taking her to see it."
The Talk: Say "I'm going with my friend Susie to have lunch with her mom, who lives in Assisted Living Paradise. Why don't you come?" Stage the whole thing if you need to, Abramson says.
The Problem: You have no clue what kind of estate planning (if any) your parents have put into place. Wills? Health proxies? Trusts?
The Plan: Ask for help with your own estate.
The Talk: Say "I'm looking at my estate planning, and I need some advice. Who should inherit my assets? What have you done to reduce inheritance taxes? I was reading an article about health proxies; do you guys have one? Or life insurance, long-term care? I could really use your expertise." Pass on articles you've read. Ask "What do you think about this? Do you think it's a good idea?"

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