My father died seven years ago. He was 93. When I was getting divorced in the late ’80s and sharing my sexual woes with my mother, she confessed to me that my father dressed up in women’s clothes, and that she never could deal with it. She wished she had gone to therapy years earlier when she first discovered it. She made me promise never to talk about it. I later found out that both my sisters knew about this as well.

As my father aged, it seemed as if he might not care if the subject was brought up: He left a makeup tray out in his bathroom, as well as nylons hanging to dry. I knew from my mother that he would get dressed up and go to the drive-through at the bank and other places. But I kept my promise. My father was always tight-lipped when it came to emotions and carried around a lot of baggage from his childhood. His mother died shortly after he was born, and his step­mothers supposedly were never very nice to him.

Since he died, I regret never having discussed this aspect of his life with him. I wonder what it would be like for him to see specials on Caitlyn Jenner, for example. I don’t really know if my father was queer, just a cross-dresser or what, but being a freewheeling bisexual myself, I hold no judgment, and I feel that if I had brought the subject up with him, our relationship might have been a closer one. Or maybe he would have clammed up more; I will never know.

Was my mother right in asking me not to mention it? My parents had a history of hiding information. For example, if one of them was in the hospital, they would say, Don’t tell anyone else. That request was easy to ignore. But what about this one? Name Withheld

My response: First, I’m sure you didn’t intend the implication, but “being a freewheeling bisexual myself, I hold no judgment” implies a correlation between bisexuality and non-judgment. Why not just say you hold no judgment, unless you believe a non-freewheeling bisexual person would more likely judge?

Next, you say your mother “made” you promise. Many people consider agreements made under duress not valid. Only you know if that applies to you.

Finally, your question: was she right? Unless you know of some book in the sky that defines absolute rightness and wrongness that I don’t, you’re asking an opinion. She thought she was right, at least when she asked. You’re not sure. Many would think she was wrong. What difference does labeling an act with an opinion make?

Since you can’t change the past, I suggest you think about what to do now. The world is different than when your father grew up. Do you want to talk to your mother or sisters about it now? What can you learn from the experience to improve yourself and your relationships today?

The New York Times response:

There’s a moral difference between keeping quiet about whether someone is in the hospital, especially when you haven’t promised to do so, and honoring a promise to your mother not to discuss something with your father. Still, if you had wanted to talk to your father about this, you could have asked your mother to release you from the promise. Or you could have told her that even though you had learned about it from her, you now also had evidence of your own (if that was the case; you don’t specify when you learned about the makeup in the bathroom, etc.) and that, with or without her consent, you planned to ask him about it.

But my suspicion — speaking not as an ethicist but as an amateur shrink — is that talking with your father about his cross-dressing wouldn’t have brought you much closer. The disinhibitions of age aside, your father doesn’t sound like the kind of person who would have wanted to discuss intimate matters with his children. When your mother made the disclosure, there was less understanding of the complexities of gender expression and identity, and so less of a context within which to discuss it. But even today, we rightly think that people should be able to decide what they want others to know about their gender identity.

My oldest brother is a financial consultant with a nationwide company. My youngest brother is my mother’s primary caretaker; she is 88 and feeble (my father, a former high-school teacher, died six years ago). As caretaker, he discovered that my older brother had created an aggressive, undiversified stock portfolio for my mother, mostly in oil and energy stocks. She even got a letter from my brother’s company headquarters warning her against such a nondiversified portfolio. One company has since gone bankrupt, and two others are doing poorly. The upshot? My mother has lost 40 percent of her savings, $115,000 and rising. One cousin, among other relatives who purchased similar stocks from my brother, apparently lost $200,000 of her $225,000. Should I or another sibling tell my sister-in-law about her husband’s disastrous stock advice? I feel that she should know about it — I don’t believe she does — first, because she’s a member of the family, and this is a family issue; and second, because it affects my relationship with her. I’m less inclined to visit her, and she should know why I’m keeping my distance. Last, and perhaps most important, her mother is in her 90s and suffers from dementia. If her mother has been subjected to the same bad or incompetent stock advice as other family members, with similarly disastrous outcomes, I think my sister-in-law ought to know that. I understand stocks always involve risk, but risk should be measured and appropriate. When the life savings of elderly folks — former nurses and teachers — are destroyed by risks that fail to consider age and station of life, it is deeply upsetting. Name Withheld

My response: First, I recommend using paragraphs.

Next, you asked if you should talk to your sister-in-law about your brother’s advice.

I suggest you change your perspective away from asking strangers yes-or-no questions about if you should or shouldn’t do something to asking yourself open-ended questions of what options you have, what resources you have, what your goals are, what results will come, how much you can improve your communication skills and other productive questions. Compassion and empathy will get you farther than judgment.

You know all these people better than anyone. You can figure this challenge out better than anyone. When you do, you’ll have the added benefit of improving your ability to handle similar challenges in the future.

The New York Times response:

You’ve made it clear that a portfolio of this sort was in no way a prudent investment for someone in your mother’s situation. Worse, if your eldest brother and his company were profiting from these unwise investments, he was abusing a position of trust. You and your youngest brother should let him know that he owes you all an apology.

Given that his actions were professionally and personally irresponsible, he’s not owed much consideration by any of you. Once you’ve told him that you disapprove of what he has done, you should feel free to spread the news widely through the family. You certainly want to protect your sister-in-law and her mother from exposure to the same risks. In talking to your sister-in-law, you won’t be the one responsible for any breach in the bonds of family: That began with her husband’s appalling conduct.

Over the weekend, my friends and I were at a party, and one of them (who had been drinking) confided that she periodically makes herself throw up, and that she has been doing this since she was a young teenager. When she told me, I was surprised, and asked if I should be worried. She said no, that all of her friends knew about it, and that it was fine. That said, I am concerned about her physical and mental health.

The next day, I wasn’t sure what to say, so I acted as if nothing had happened. She said she didn’t remember a lot of things from that night; I’m not sure if she recalls telling me about her situation. I’ve also noticed that her attitudes about food, dieting and exercise seem misguided and compulsive, and that she needs a lot of validation about her appearance. I didn’t think these things were a big deal, but now I’m afraid they might be signs of something more serious.