ArcaMax

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, 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.

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