Honesty is the way to go

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, though I knew she existed through the duration of my friendship with 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 full-on and successful relationship could lead to a great future. How do I navigate this?

Conflicted in PA

Dear Conflicted: If you want to preserve your friendship, you should make your friend aware of your friendship with his daughter. It is somewhat surprising you didn’t do this earlier.

I intuit that there is a complication you are not revealing — perhaps father and daughter are estranged.

Regardless, she contacted you because of your friendship and connection with her dad, and I’d say that no matter what, he is already a character in your story.

You should start by saying, “I received a message from ‘Candace,’ and we’ve been in touch. I just wanted you to know that.”

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.

Of course, there is a possibility that he will react very poorly, 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 may require some discretion and healthy boundaries on your part.

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

He was happy to hear from me and we swapped many emails, although only when I sent him writing samples, which he said he enjoyed reading.

I asked to see samples of his work since I was sending him mine, but he didn’t.

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?

Not Well Read

Dear Not Well Read: Your former teacher seems to have been very kind to you.

He may not have any writing samples to send to you. He also might have health problems of his own.

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

Find an online or in-person writing group with whom to share your work. The critique and feedback can be very helpful.