My beautiful 23-year-old great niece has very bad teeth especially wisdom teeth. I believe her life would change dramatically for the better if she had cosmetic dentistry. Twice I’ve gently mentioned to her that I would be happy to pay for it and to go with her if she didn’t want to go alone. Both times she got upset and I quickly changed the subject. Should I keep pushing? Should I leave money in my will specifically for this purpose?

Concerned Aunt

Dear Concerned,

When I was about 35, I met a guy who told me he hadn’t once brushed his teeth as a child. He was a husband and a father, and a successful small businessman. He had lots of friends. And though he said he’d started brushing as an adult, his teeth were a gray and slimy affront to good old American dentistry.

I was shocked that he had never brushed his teeth as a kid, but I didn’t give him my dentist’s number and he didn’t ask. I just figured that, for whatever reason, he was an adult and it was his weird burden.

I thought of an old Rodney Dangerfield line: “I told my dentist my teeth are going yellow. He told me to wear a brown tie.”

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Your great niece also is an adult, though naturally it’s easy for you to think of her as a kid. We all do that with younger family members. I am touched by your concern for her, because I too was fortunate to have had a great aunt who cared deeply for me, and helped me out at various times with both advice and money.

However, the most valuable gift she gave me was unconditional love at a time when my nuclear family was detonating. That kind of love could also could be your greatest gift to your niece. The bad teeth could be the result of many issues. She might be afraid of dentists. Her parents might never have taught her how to take care of herself. It might be that she's suffering a difficult-to-treat eating disorder and doesn't want to fix her teeth until she’s got it under control.

What’s certain is that she heard you say her teeth would look better if she went to the dentist for cosmetic treatments that you would pay for. You know she heard you, because she got pissed off at you. There’s no reason for you to say it a third time. Do not beat this dead horse just because you led it to water but couldn’t make it drink.

I do like your idea of leaving her enough money in your will to cover the cost of getting her teeth fixed or use cosmetic dentistry to not be under clinical depression. If it were me, however, I would leave the money with no strings attached. She’ll be grateful, and she’ll know that you would probably have liked her to use it for her teeth. But maybe she’ll have something more important to spend it on that you can’t predict. And you probably won’t be too concerned about her teeth once you are dead.

My best advice is to love this young woman, and stand by her no matter what her teeth look like. She probably needs some loyal friends right !!