We are a large family, and our father is in his 80s. Our mother died several years ago, so our father moved into an upscale retirement community. A handsome, successful, charming gentleman with plenty of money in the bank, he was an instant hit with the ladies. From the beginning, he was seriously pursued, but he always kept it light.

Two years ago, a manager of my dad’s retirement community began to single him out for special attention. She is in her 60s, flirtatious and attractive. She dresses stylishly, and in many ways she reminds us of our mom: upbeat and vivacious.

At first, we were pleased that Dad had someone in his life. They would go to lunch or dinner two or three times a week; Dad paid for everything. Sometimes we saw them giggling like kids in the hall. It was nice to see Dad so happy. We know he missed our mom. There was just one snag: The retirement community prohibits dating between residents and staff members. So Dad and the woman kept their relationship secret.

Last year, Dad found out he had cancer. The woman seemed devastated. She started to drive his car when they went on dates, because Dad is too medically compromised.

Well — and you knew this was coming — as we’ve learned more about her, we are becoming concerned. First we learned that she has been married several times. Then one day, after my father picked up some OxyContin pills for his cancer pain, she exclaimed that she could use a few of them for her own pain, and my dad gave her a handful.

This was bad, but it got worse. Dad has confessed that she now “wants more” from the relationship. He says he’s “stalling,” but who knows what that means? I thought about reporting the woman to her employer — asking a resident for narcotics seems like a gross ethical violation — but my dad, being a gentleman, would claim that he offered them to her or maybe even deny it happened. And it may all be moot, because next month she starts a new job several miles away. (She plans to drive over to see Dad often.)

Our dad is not isolated. All of us children visit frequently. He has hundreds of email friends and exchanges multiple messages every day. He has old colleagues who come to take him to lunch. But none of us can provide the delightful frisson of romance. We know that. I wish I thought this woman really loved my dad, but I don’t. In fact, last month an old friend of the family, who knows both my dad and the woman, asked if she had “gotten any money yet.” Apparently this man once dated her, and yes, she asked him for money, and he gave it to her.

I do think she really likes Dad and maybe even cares for him. But I also think she sees a payoff. My dad is a smart, pragmatic guy, but he’s close to 90 and a bit confused at times. He is more vulnerable than he knows, and I worry that she might be pressuring him for money or even to change his will. He has shared his will openly with us in the past and was generous to us all. But it has been a year now, and he says only, “You will all be taken care of.” We’re in our late 50s and 60s, so such a promise is meaningful. But given her age, the woman is also looking at her own retirement. And given the life she has led, it’s conceivable that she might view Dad as her last chance for a payday, especially now that he is starting to have cognitive challenges (which he would deny).

Dad admits that she “has a lot of problems.” We suspect that some of these problems involve money and that, being a gallant man, Dad might be tempted to solve them.

We tease him about being the next husband, but we are seriously scared that if the infatuation continues, and she will do her best to see that it does, she will manipulate him into changing his will or we could find ourselves with a new stepmother. Nobody wants to hurt Dad, so we say nothing. What is the ethical thing to do? Name Withheld

My response: Most of my responses take for granted the people involved are adults who can decide for themselves based on their values. If you father is one of them, I don’t see why he can’t do what he wants with his time and possessions. I suggest people consider the results of their actions on others. If how his actions affect you doesn’t affect him the way you want them to, you can try to influence him, but I don’t see what more you can do.

As usual, I suggest your question of what the ethical thing to do is, is masking your intentions and confusing you. You can let him do what he wants and few people would question your ethics. Your problem, as I see it, is that if you do that, you’ll lose some of your inheritance and he’ll do things you wouldn’t. Why do you call her influencing him to change his will “manipulation” but you expect your influence on him “the ethical thing to do”? If so, I suggest you be more honest with yourself that you’re concerned for your interests. In that case, your question isn’t what’s ethical but how do you influence people along your interests while building relationships, not undermining them—what some call leadership, or at least a part of it.

If that’s your goal, I suggest you learn to lead more effectively, then apply your skills. Not to promote my materials gratuitously, the reason I created my leadership course is that I believe it’s the most effective way to learn to lead, certainly more than every traditional information, lecture, and case study based course or book I’ve seen.

If he’s unable to decide for himself, just find some lawyer to get control of the rights he lost and act unilaterally. You sound like you’re thinking about it. It doesn’t sound like that’s the case, though, just something you’re implying to justify meddling in his affairs that put your money at risk.

I’m not saying I like his decisions, though I only have your views on them. Just that I support people doing what they want within rights everyone agrees on. I also support you doing what you want, including influencing him. I think you’ll get farther being more open about your interests and developing more skills to act with empathy and compassion.

The New York Times response:

Life seldom gives us the sharp lines we look for. In particular, as we get older and our cognitive capacities fade, there’s no sharp line between being able to look after ourselves and needing other people to take over. Your father sounds as though he is approaching that transition, while remaining on the better side of it, at least most of the time. So you can surely take these issues up with him. Have you told him all you know about his friend? You don’t say. If you have, he may well think that you’re just wrong about her motives. And he does, after all, know her better than you do. It is worrying, I agree, that she has been breaching the terms of her employment and taking some of his drugs. But reporting the dalliance to her employers or the OxyContin episode to the authorities would be profoundly disrespectful to your father.

In relationships, of course, the truth matters. However much fun they have together, there’s something badly wrong if she is thinking of him fundamentally as a source of funds and he doesn’t know this. But fun matters, too, and your father could be willing to accept her attentions while knowing that her affections are tinctured by venal motives. If that is the case, they may each, to some extent, be playing the other.

What about your own motives? You express two related concerns: that his will may be changed in a way unfavorable to you or that you will end up with a new stepmother. But while your father is compos mentis, each outcome is within his legal and moral rights. (If he isn’t competent when testamentary decisions are made, you can challenge the will.) As for dealing with a new stepmother? Given that, as you suggest, they are happy together, she is unlikely to try to keep you away from him. So there’s no reason to doubt that you can continue to play a loving, supportive role in his life.

I am a 52-year-old professional who recently began wearing hearing aids to assist with mild degenerative hearing loss. The devices are fairly inconspicuous, but even so, they occasionally cause raised eyebrows and what I, at least, register as pity. (It’s surprising that when someone my age wears glasses, it doesn’t get the same negative reaction.)

I am contemplating a career move. Would it be ethical for me to interview without wearing the hearing aids so as not to harm my chances of securing a new job? My hearing is obviously better with the devices in, but I’m willing to forgo them if it will help me land a new position.