Do I Take A Chance On This Man?

Friday | April 8, 2022

Love Letters Dating

Do I Take A Chance On This Man?

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Hello Meredith,

I am a professional, divorced woman, early 60s, trying to meet an intelligent, kind, non-pretentious man for a serious relationship.

There was a man I dated for almost two years – I loved him – but he repeatedly wasn’t candid about his situation, and cancelled plans with me often. When I asked for clarity, he told me I misunderstood and emphasized how he was always the victim in his life’s circumstances.

I stopped attempting to understand his victim mentality and ended the relationship. Several years later, I have met an intelligent, kind, unsophisticated man who is quite sincere. I probably have more financial security than he does, however, he is hard-working. Neither of us has plans to retire. Do I take a chance on this diamond in the rough or just let go of the notion that I will meet someone?

– Not Typically the Risk Taker

It sounds like you’re excited about this new person. You believe this man is sincere and kind. You think he’s smart.

My question to you: Why wouldn’t you pursue it?

If you were feeling lukewarm about the whole thing, I’d say give it up. Maybe take a beat and consider what else is out there. But this particular man seems to be the kind of person you want. You do seem hopeful.

Maybe this is about the finances – that he doesn’t have what you do or more. I can’t tell you money doesn’t matter, and only you understand your own needs. If you were hoping for a partner who might help make retiring easier, well … that’s something to be honest with yourself about.

But you do not list money as a priority in your first sentence. Think about why.

Really, all dating is a risk. You either want to be open or you don’t.

You say you want something serious. It does sound like you’ve found a good candidate.

– Meredith

Readers. I’m rooting for this one and think the hesitancy is about the last relationship. Where do you stand?

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