Amy: Newly single guy is conflicted

  • Article by: AMY DICKINSON
  • August 17, 2013 - 2:00 PM

Dear Amy: Three months ago I called off an engagement and have finally been able to move on from that relationship.

I decided to ask out a woman who has been in my life for some time. She always hesitated to date me because of my colorful past, but she finally agreed to a date.

The same day she told me that she was ready to give it a shot, I met an amazing woman, and I can’t stop thinking about her. We have similar interests and backgrounds, but there are a lot of unknowns.

The first woman is a terrific woman from a great family, and I’ve been trying for years to get her to go out with me. I am not sure what to do. I don’t like the idea of seeing both women at the same time; it just doesn’t seem moral to me.

Amy says: You mention having a “colorful past.” Oh, how I wish you had filled in a detail or two!

The way to handle this is to be transparent. This means that when you ask out “Woman A,” you invite her to be your dinner partner, not your relationship partner. The same goes for “Woman B.” Don’t plunge headlong into sexual/emotional relationships with these women. Get to know them. Then make a choice about what you want and whom you want to be with — and hope the person is also interested in being in an exclusive relationship with you. You are just a few months removed from a near-miss. Be cautious, careful, honest and kind to any woman you are getting to know. Take it slow.

Parking problem

Dear Amy: I wonder about the etiquette of parking. I live in a small town that does not have a lot of traffic. My neighbor — who lives across the street from me — parks in front of my house all the time. She has only one vehicle, as well as a driveway, and there is never anyone parked in front of her house.

It annoys me that she is always there.

I know this sounds petty, but when I sit out on my front porch, I don’t want to have to stare at her car. Should I mention to her that it bothers me, or will that make me seem like a weirdo?

Amy says: This annoys you because ... it’s annoying. Your neighbor parks in front of your house because she doesn’t enjoy the view (of her car) when she parks in front of her own — she may also find it challenging to back out of her driveway. You are not a weirdo. Approach her, introduce yourself and say, “Could you park in your driveway or in front of your house? That way I could see more of the street from my porch. I appreciate it very much.” You can’t force her to comply, but you do have to be brave enough to ask.

Send questions via e-mail to Amy Dickinson at

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