I’ve been friends with “Cindy” for 15 years. She’s in her early 60s and never married. Because of job stress, she took early retirement and lives on a reduced pension. Despite not having a lot of money, she is generous, spoiling her family and friends with gifts.

Two years ago she became romantically involved with a man, “Sean,” who was bankrupt and homeless. He started staying with her right after they met. Cindy reveled in having a lover for the first time in 30 years. Sean helped her lose weight and exercise. However, he is a complete loser in my view: Not only does he rely on her for his cash, transportation and cellphone needs, but he is also habitually drunk by 4 p.m.

More than a year ago Cindy started using what credit she has to start a business with Sean from scratch. She is spending thousands on manufacturing, shipping and storage and long hours hawking and doing administrative work. There’s no indication that they are making any profit; she admitted this and said she would give it one year, but she is now saying two. Cindy’s life is endless work and financial outlay — the conditions are worse than what made her want to take early retirement.

I spoke to a mutual friend about my fears for Cindy’s financial future. She agreed that Cindy might go bankrupt but pointed out that Cindy does have a mortgage-free home. So I’ve remained silent. Recently I found out Cindy was recovering from a minor stroke. Her fridge was almost empty, and I could see the bloom had worn off the relationship with Sean. While he chided her about her eating habits, she complained of his constant drinking.

When he moved in with her, she seemed cautious; she talked about how in the province of our country there is a legal entitlement to spousal support after cohabitation for three years. As this date approaches, I am racked by the belief that I must do something to help her break free. I thought of contacting her siblings, with whom I have no relationship, to see if they would consider some sort of intervention, but should I mind my own business? Name Withheld

My response: I can’t help starting by commenting on how juvenile your question on what you should do sounds, at least to me—that is, I could see a child asking a parent for help understanding right and wrong, but I’d expect an adult to develop that sense.

But asking for judgment is beside the point. I expect you’re asking because you don’t know how effective you’ll be. If you knew Cindy would appreciate your views and advice, even if she disagreed, you would intervene.

I expect you’d find answers to questions like, “What options do I have and how effective would they be?” or “What skills can I develop to increase the chances of Cindy appreciating and valuing my intervention?” more valuable, instead of thinking of one option and deciding yes or no about it.

I recommend thinking of those questions, to open up the range of possibilities and motivating you to solve problems and improve your social and emotional skills instead of asking for judgment.

The New York Times response:

This is a sad story, and in its outlines, alas, not an unfamiliar one. Given that Cindy is a mentally competent adult and a friend of yours, though, the obvious person to talk to is not a sibling of hers but Cindy herself. I don’t mean that it would necessarily be wrong to express your concern to a member of her family. But to do so without first talking to her would be disrespectful. If she insists that you not talk to her family, you should take her wishes seriously.

The modern ideal of autonomy means that we think each person should be in charge of her own life. But this doesn’t mean that friends and family should avoid stepping in: Advice given out of love and concern for us is no affront to our autonomy if it helps us think through our situation more rationally.

All that granted, it’s hard to intervene in cases like this. You’re asking someone to let you talk to her about a situation that is probably a source of shame. If you really think that he’s just taking advantage of her, though, the time to speak up is now. It’s what friends do.

Many years ago, a dear friend of mine told me she engaged in behavior I consider abusive. She was a high school teacher. She got drunk and took pills with two recent graduates (both 18) and then engaged in a cutting ritual with one of them. They spent the night in bed “cuddling” to comfort each other over the cuts they’d inflicted. She found it a very arousing experience. I reacted strongly, told her she could go to jail, that she had to quit her job, that she could no longer be a teacher. She kept insisting it was O.K.: The girl was 18, and it was consensual. I had a moral impulse to tell her principal, but in my loyalty to her, I did not. Nothing happened. She kept her job and never expressed much regret. Her lack of responsibility infuriated me, and our friendship fizzled. I was left with the moral discomfort of failing to report her.

Recently, she wrote to me because she is suffering from a degenerative disease and wants to “make amends in case anything happens.” She also says she has dissociative identity disorder, which I am not surprised by. She mentions a few things that happened between us that she regrets, but nothing about the cutting incident. I forgive her for all these other things; there are things I could ask her for forgiveness for, too. The one thing I can’t get past is her taking no responsibility for abusing her student. My question is: Is it ethical for me to bring it up? She is sick, and now officially mentally ill. She may have suppressed the memory. Could bringing it up be a dangerous trigger? Is it ethical to confront a mentally ill person about an abuse she committed years ago when the abuse had nothing to do with you? Name Withheld

My response: Same answer as to the first letter, with obvious changes.

Instead of asking for judgment on few options and closing yourself off to more effective ones, I’d recommend asking for ideas for more options and figuring out if the ones you consider best pass a threshold of effectiveness.

You didn’t ask, but I also recommend developing your emotional skills to handle the fury and moral discomfort you feel. I expect that those feelings won’t help your interaction, nor your life, hers, the students’, or anyone else’s. You can justify the feelings, but if your goal is to help others, I think you’ll help them more after developing other emotions.

The New York Times response:

I agree that your friend’s behavior sounds worrisome. But I don’t see that it was wrong merely because the other party had been a student of hers. Once a student is an ex-student, and outside the relationship of trust that exists between teachers and students, sexual or semi-sexual acts like these are the business of the participants — provided there is full consent. When pills and alcohol are involved, consent can be hard to establish. And of course, in all relationships, there can be forms of power that it is abusive to exploit. If any of that was the case here, what happened was wrong. Was it illegal? When it comes to state intervention, the critical questions are: “Was one of the parties in a position of authority or trust over the other?” and “Was there genuine consent?”