I have been single for over a decade and want to start dating again. During that time a gentleman I’ve known for many years asked me out. I said no. I was not ready to date anyone.

Fast forward a few years and I am ready to date after some soul-searching and counseling. The same gentleman wants to date me, but I have two concerns. First, he just got out of a relationship a few months ago. I do not think he is over it. Second, I am a very slow-moving person and voiced my concern that I want to know if our lifestyles are compatible.

He seemed irritated by that, and I saw a post on social media referring to the one phone conversation we had. We also flirted across social media once. I only want to date if it feels right and makes sense.

Not sure, though, if I should inquire further or walk away. I do not want to be hurt again. This sounds like high school to me, but perhaps I have missed something here. I just don’t know. Your thoughts?

~ Amelie

Amelie, the central character in a famous poem by T.S. Eliot is named J. Alfred Prufrock. Prufrock is a man with huge concerns over small anxieties. At one point, he says, “I have measured out my life in coffee spoons.” At another, he admits he has time for “a hundred indecisions.” The poem ends with Prufrock asking himself, “Do I dare to eat a peach?”

J. Alfred Prufrock did not understand the nature of life. There are no guarantees, no sure things. We can’t take a job, enter a store, or order a meal with a guarantee we won’t be disappointed. Our car can fail us.

For at least a decade you haven’t dated. You were so traumatized by something you’ve been out of the saddle for a long time. That length of time was probably not helpful.

You want to put a precondition on life: I don’t want to get hurt. But to enact that precondition, you must be able to predict the future, a thing no one can do.

When you asked about this man’s lifestyle, he was miffed. “I asked for a date,” he thought, “I wasn’t applying for a top-secret security clearance.”

If you need him to fill out a form in advance, he won’t accept that. It is not his temperament. As creativity expert Gerard Puccio says, “Looking for 100 percent guarantees of success will always stop us from pursuing something…”

Ultimately, what are you saying? I only will date a man who will marry me and be the fulfillment of all my dreams. That’s not realistic. Paralysis by analysis is no fun.

You want to find out more about him? That’s what dating is. The process of learning more about another to see if we want to continue. The first issue in dating for a woman is physical safety. Once that need is satisfied, who knows where it will go.

Trying to find your one, there will always be some heartache, some pain, some disappointment. Who hasn’t been on a so-so date or an awkward date? But consider this. You are already disappointed. You don’t have anyone to date, and you are alone.

Someone said, if we are living in the past, we are dead to the present. J. Alfred Prufrock would not dare to eat a peach. Do you dare to try, even though you know it may not work out?

~ Wayne & Tamara

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