Ask Amy: An unusual take on a romantic triangle

Dear Amy: I have a very close friend who is 30 years older than I am. We two men have known each other for years. He is like a surrogate father to me, and I cherish the friendship immensely.

His daughter, who is my age, recently reached out to me over social media. She and I had never met, even though I had heard a lot about her from her father.

We went out. We had great chemistry, and we continue to talk. It's been wonderful. I am very intrigued by her, but I am conflicted. I want to see where this goes, but I'd hate to compromise my friendship with her father. It would be devastating to me for it to end.

But I also feel a genuine connection to his daughter, and I think a successful relationship could lead to a great future.

How should I navigate this?

Amy says: If you want to preserve your friendship with the elder man, then you should make him aware of your new friendship with his daughter.

In fact, it is somewhat surprising that you didn't do this earlier. I sense that there is a complication you are not revealing. Perhaps the father and daughter are estranged, or their relationship is strained. If so, I have to wonder about her motivation in contacting you.

If he has misgivings about this contact or about you pursuing this relationship, he will have to reveal his feelings to you. You should prepare yourself for a possibly awkward period of adjustment for all of you.

But if you aren't honest and he learns about this later, there is a far greater likelihood that he will question your integrity and feel embarrassed and misled — by both of you.

Once you've revealed the friendship with his daughter, there is no need for you to disclose the particulars. Keeping both relationships positive might require some discretion and healthy boundaries on your part.

If the relationship with the daughter "goes south," you will have to try to do what many people have done, quite successfully, which is to work hard to maintain an ongoing friendship with her dad, while respectfully parting from her.

Dear Amy: I am a writer. Sometime ago, I tracked down my high school English teacher, who always had been very supportive (decades ago).

Then I told him I was going to have surgery. He did not respond to that, send good wishes, or follow up.

I gave up, but I miss having someone to discuss my writing with. Should I reconnect and accept the one-sided friendship?

Amy says: Your former teacher seems to have been very kind to you.

It does not seem to have occurred to you that he doesn't have any writing samples to send to you. It also doesn't seem to have dawned on you that your teacher might have health problems of his own.

Yes, I suggest that you keep in touch, just to check in. Catch him up on how your surgery went and ask about him.