Ask Amy Amy Dickinson, Ask Amy

Amy Dickinson is a general advice columnist.

DEAR AMY: I am a woman in my late 60s who has had a friend for more than 40 years. Many years ago I was in a powerful position with an organization and encouraged her to apply for a job with the company. She worked for several years in various administrative roles (never reporting directly to me) and was a very good employee, as well as a good friend. We stayed friends even after she moved away. I’d always invite her to join my friends and me at all my parties and ticketed events. She and I even traveled on several trips together. I sensed her distancing herself, but I didn’t push it. Last year I had a short visit with her. I thought we had a decent time. Then, about two weeks later she called and told me something her therapist had told her to tell me — that she didn’t like to travel with me because I was too bossy. I told her I thought hers was an easy problem to solve; we just don’t need to travel together. I then tried to find out if there was anything else bothering her about me, and she said no. I tried to be calm and remain friendly. We seemed to end the conversation on a good note, but since that time I’ve not heard from her at all. I am confused and hurt. I’d like to let her know how hurt and angry I am about her complete dismissal of me and our friendship after all these years. I believe she owes me an explanation. What do you think I should do? Upset

DEAR UPSET: Generally, when someone tells you she has discussed your relationship in therapy, it’s not a good sign. In this case, your friend told you that you are too bossy for her and you responded immediately by telling her you could solve her problem in a way that seems — if not bossy, then definitely dominant.

The response she might have been hoping for would not be, “You have a problem. I can solve it,” but, “Oh, let me examine my own behavior and see if I can change it.”

For your friendship to revive it would be best if you asked how she would like for things to change, without telling her what to do.

DEAR AMY: I am moving back to my hometown and starting a new job within a couple of months. It has been nearly three years since my last relationship and I feel like I can start interacting with women and dating again. My last relationship was very heartbreaking. I began reconnecting with old school friends (back in my hometown), especially one woman I’ve known since high school. She is a single, full-time nurse at a hospital. Last month I “anonymously” sent her chocolate-covered strawberries to her workplace and she posted it on her social media, saying how happy she felt. I have yet to tell her I sent the gift because I don’t want to come off as a creep while trying to reconnect with her. I really would like to do that in person. I don’t want to make her uncomfortable. Do I tell her about the strawberries when I message her? What should I do next?

Man on a Mission

DEAR MISSION MAN: You haven’t said whether you have already disclosed to this old friend your plan to move back to your hometown, but doing so is the right way to feel her out about a connection.

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If she responds by saying, “That’s awesome, I’m happy for you,” then you should not swoop in aggressively. If she says, “Great! Let me know when you get here. It will be fun to get together,” then you should read that as some interest on her part.

I agree that anonymous gestures can sometimes seem creepy. Don’t make assumptions about her interest unless she clearly telegraphs it, and don’t disclose this gift until you are convinced she is interested in you, waiting until you have seen one another in person.

DEAR AMY: I’m disappointed by your response to “Sad Dad,” whose parents had mistreated his wife over the years and now, after a lengthy estrangement, he wants her to find a way to “look past it.” He should man up and stand by his wife.

Marry an Orphan

DEAR MARRY: This reader wanted to find a way to try to reconcile, not continue an estrangement. I offered him ideas, but I also think his wife should not be compelled to spend time with people who have mistreated her.