Ask Amy: Should I date my close friend’s daughter?

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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 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 in any way. It would be devastating to me for it to end.

The thought of losing my friend in the short or long term in the event that this goes south is hard to face.

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

How should I navigate this?

Conflicted: 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 intuit that there is a complication you are not revealing; perhaps the father and daughter are estranged, or their relationship is strained.

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

If the relationship with the daughter “goes south,” then 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. 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 emails a lot, although only when I sent him writing samples, which he said he enjoyed reading.

I asked to see samples of his work, because I was sending him so many of mine, but he didn’t send them.

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: 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 (who is at least 25 years older than you) might have health problems of his own.

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

You should find an online or in-person writing group with whom to share your work. The critique and feedback can be extremely helpful.

Dear Amy: A weird question, perhaps, but I often find myself very moved and concerned by the questions I read in your column, and although you are frequently funny, I do find myself tearing up.

My question is: Does your work make you cry?

Wondering: Yes, most days. I anchor to the long-ago wisdom of the great Ann Landers, who said something like: “I can’t take on other people’s problems. I’ve got enough problems of my own.”

©2022 by Amy Dickinson distributed by Tribune Content Agency

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