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The question

After a long (almost 25 years) and unhappy marriage (my ex had substance-abuse issues and was abusive) and difficult and costly divorce (in more ways than one), I’m single again in my late 40s and gradually rebuilding my life. My friends and family are nudging me to start dating, but I’m really worried that, given my lack of experience and poor track record choosing a partner, I’ll make another bad choice. How will I know I’m ready to date and how can I learn to trust myself?

The answer

I’m so honoured and also so challenged that people would put such thorny and difficult questions at my feet.

It would be easy to say “follow your heart” or “you’ll know when it’s the right guy” or some such bromide/platitude.

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But we all know, or at least I do, someone who was with the wrong person, maybe even had a kid or two with that person, broke up, then got back in “the game/out there” and finally met another person – who turned out to be even worse!

What I’m trying to say is I think your fears are legitimate.

And what you’re really asking me is threefold: 1) Would it be better to be alone than with another terrible guy? (yes) 2) Am I ready to go through the whole dating grind? (sucks) 3) How will I know if one of the guys I wind up dating is “Mr. Right”? (tough)

Let’s set aside the first two questions, or at least assume that, like me, you wouldn’t mind a nice warm shape in bed next to you and are brave enough and willing to get “out there” to find one.

How do you know if you select one he won’t put you through the mill again?

Well, as Hamlet says, “Ay, there’s the rub.”

Let’s assume you’re looking roughly in your own age category: late 40s. Well, if a guy is still single at that age, obviously the question becomes: “What’s going on there?” Is he commitment-phobic, addicted to the swinging single lifestyle, a “rogue elephant”?

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(I mean no offence to those who make the deliberate and conscious decision to remain single: it’s just she’s looking for a partner – maybe.)

So basically you’re looking at a pool of divorced dudes. In which case the question becomes: “Why?” Why did they divorce?

If I were you, I’d listen carefully to that story. It’s just possible the divorced dude is a good person (like you, it sounds) who made a bad choice and wound up in a bad situation – and you might be able to snatch up that good person and have a happy life together!

But there are warning signs I’d watch out for. Does he blame his ex exclusively for everything that happened, or does he accept some of the responsibility himself?

I’m always leery of people who say, in effect: “My ex was a terrible person and everything that happened was all his/her fault.”

My response is always: “Well, at the very least that makes you a poor judge of character, doesn’t it?”

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And in the end that’s what you’re really asking me is, isn’t it? “How do I judge another person’s character?” Which is obviously a terribly difficult question.

I’d say “rely on your instinct" but as you’ve experienced, and, sounds like, intuited, one’s instinct can often lead one astray.

I’d say “check his history” but that can also be fantabulated, if that’s a word (not according to my computer: but anyway, let’s make it up), in other words you should not believe everything he tells you about himself.

If at all possible I’d get third-party confirmation/denial of whatever this dude tells you. Easier said than done, perhaps. My aphorism as a teenager was always: “Women compare notes. So if you want to date one of them, you have to impress them all.”

But I know it’s harder to find people to compare notes with in your late 40s. However, if you can find anyone who can vouch for your prospective suitor, that will help your cause.

Above all, I would say, take your time. Be patient. Eyeball anyone you wind up interested in from all angles before getting involved. “Fools rush in” and all that, and you don’t want to waste another 25 years.

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Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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