DEAR AMY: I am a woman in my early 30s. I haven’t had many successful relationships. Lately, whenever I meet someone I’m interested in, it lasts less than a month. I met someone last year at an event through a professional organization. He is a distinguished politician who had recently gotten out of a long-term relationship. We had some friendly conversation. Over the next couple of months, he helped me with another project, and we had some mainly professional chats. I had a mishap with some text messages — once I messaged him instead of my mom, and he jokingly called me a dork. Another time, my friend sent him some very “forward” texts from my phone. I immediately apologized, but he seemed to withdraw. I recently found out that he is registered on an online dating site. I want to try to connect because I feel that we could hit it off, but I don’t want to risk scaring him off again. I just think that if he knew the real me, he would like me because we got along last year — before all the awkwardness happened. There is another event through my work (off-work hours) that I can invite him to, but I worry that it will be strictly professional again. Any advice?

30-Year-Old Teenager

DEAR TEENAGER: The phrase “strictly professional” gives me pause. When, in your experiences with this person, have you been even slightly professional?

OK, sending him a “mom text” accidently could have been the start of an adorable “meet-cute.” But your friend sending him “forward” texts from your phone (I gather that these were obnoxious, romantic or possibly sexual) likely locked you out of having a relationship with him. He withdrew from you because he graduated from high school some time ago, and who needs that kind of nonsense now?

I assume that your behavior toward him has made your interest in him quite obvious. There is nothing wrong with that; being “out there,” obvious and authentic is not a bad thing. But you need to read and respect his signals, too. He has your number. He knows you’re interested. He’s obviously looking. If he was interested in you, he would have contacted you.

You could either register on the dating site or invite him to your after-hours work event. If you have any contact with him, this time, try to actually act “professionally” (relax, don’t reveal too much, discuss neutral topics), and see if you can reset your dorkometer.

The bigger question concerns your own dating behavior. Read India Kang’s book, “How to Date!: Single Girls’ Dating Manual (2016, YouCaxton Publications).

DEAR AMY: A co-worker and I share a good friendship. One of the things that bonds us is that we have both been through prostate cancer. While I am still clear, it looks as though his is coming back. He is OK and has the support he wants and needs from his family. Our challenge is a desire to help others. We would like to do what we can to help alert other men to the need to monitor their health and be informed. While each of us is prepared to share our story (if asked), we are reluctant to volunteer it. We are not interested in expressions of concern or sympathy. We don’t want to become “poster children” with a lot of focus on us. Do you have any suggestions on how we might navigate through this, calling attention to the issue, but not ourselves?

Private Guys

DEAR GUYS: This is the first step! Thank you so much. I hope that your query will inspire men to be tested and to support one another. You and your friend can be a great resource to other men — without drawing attention to yourselves.

Check out the work of the This support group of prostate cancer survivors was started by five men in Chicago, and now has grown to a supportive national community. Join an online or in-person support group to communicate with other men who are going through this health challenge.

DEAR AMY: Thank you for running the question from “Not Singing in Middletown, R.I.” This person mentioned being chastised for looking at her phone during a theater simulcast of the Metropolitan Opera. What I appreciated the most was when you corrected her for referring to the stagehands as “maintenance workers.”

Opera Fan

DEAR FAN: These skilled stagehands are very much part of the production. I love watching the set changes.


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