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Go on, go back to your Bad Boy. You know you wanna

The question

My boyfriend was, is, a wonderful young man of 42. We were together once before, for five years, when he was 22 and I was 30. We kept in touch then got together again after I called him on his 40th birthday to find he was divorced. I should add that he was and still is my favourite lover of all time. That was two years ago. We started seeing each other regularly, without any strings attached. One day he surprised me, asking if I would be his girlfriend and would I consider moving out of the city to live with him. We were seriously looking into this. Then he casually mentioned that on weekends he was sleeping with a woman who lived outside the city. He had been sleeping with her for a while. Now, I have to mention that he's handsome, funny and smart. I knew he probably wasn't 100-per-cent faithful to me, but I didn't know he had a whole other relationship going on. I told him I couldn't do this any more and asked him to leave. Now I miss him and the life we almost had together. Everyone in my circle says good riddance, but none of them make me laugh, think or feel the way he did. Is there anything here worth salvaging or should I just hold my head high, knowing that I did the right thing?

The answer

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Of course, it'd be easy for me to tell you, like your friends, to walk away.

That would be the sensible, commonsensical thing to do. Clearly, this guy has only very hazy, underdeveloped notions of monogamy; and seems quite immature for a "young man" of 42.

And yet … when you say he's your favourite lover ever, that he makes you laugh and think and feel like no one else - it almost sounds as if in your eyes everyone else seems boring compared to him - it gives me pause before advising you kick him to the curb.

I think you're experiencing The Lure of the Bad Boy, a bit, here, madam.

It's a powerful force, is it not, ladies? It hai-karate-chops your higher functions; disables your ratiocinative powers like a cat-burglar disarms an alarm; and hot-wires your libido.

You know if you get together with the bad boy - or back together with him - you're probably making a mistake: that he will almost certainly disappoint you in the future as he has in the past.

But you cannot help yourself. You are drawn into his vortex against your will.

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To be honest, I thank God for this phenomenon every day. Otherwise I could never have hoped to snag, tag and bag a woman so manifestly out of my league as my wife, Pam.

When we met, I was, if not a full-on, wheelie-popping Hell's Angel, at the very least a rather naughty fellow. I lived above a store in a part of town some considered sketchy, others downright dangerous; wore my long hair slicked back; was tanned, lean and mean; smoked a fair amount; only had a part-time job - and wasn't even looking for work!

Undateable, to some women's way of thinking. But Pam - responsible, goody two-shoes suburban banker's daughter that she was - was drawn to my bad-boy mojo like a June bug to a fly-zapper. Zzzzt! One sultry, summer night, her chances of marrying a decent, upstanding citizen were incinerated in a flash.

(Worst mistake she ever made, in an otherwise purposeful and well-organized life: Luckily, 3 kids and 18 years in, she still doesn't seem to have clued in to that fact!)

Sounds like you've got something similar in the works with your "young man."

And now I'm going to metamorphose, perhaps, from bad boy to bad advice columnist (imagine me skidding to a stop in front of you in my Harley, popping off my helmet, and firing up a cigarette as I say this) when I tell you I think, from all you've told me, maybe you should look into getting back together with this naughty fellow.

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Of course, prudence dictates you walk away from this troubled pas de deux. But what do prudence and love have to do with one another, really? "Le coeur a ses raisons que la raison connaît point," as Pascal said.

Sometimes great relationships can grow from circumstances that don't look too good on paper. And sometimes, these aging Lothario/bad boys surprise everyone by evolving into good husbands and fathers.

The trick is to catch them just on the cusp of saying "Uncle, I've had it with tom-catting around, I want to settle down" - like Warren Beatty did with Annette Bening.

(Though I think he was somewhere around 60 before he hung up his bachelor spurs.)

Then you get it all: decent, stable partner who also pushes your buttons and makes you laugh.

If you do go this route, though, no more of this "no strings" stuff. That was your biggest mistake, it seems to me, in the last iteration of your relationship.

Give him strings! Read him the riot act: If he wants to be with you, he has to straighten up and fly right. No more Mr. Casual: "Oh, hey, I'm sleeping with this other chick, too."

Now, the Canadian Society of Advice Dispensers (CSAD) would revoke my licence, or at least levy a stiff fine upon me, if I didn't say at some point that if you do choose this option, you should brace yourself for disappointment.

Naughty fellows change their stripes - sometimes; more often not. In all likelihood, getting back together with him will be a mistake. It's just that, the way your letter is worded, and from what I'm reading between the lines, it sounds like it's a mistake you'll wind up regretting more if you don't make it than if you do.

David Eddie is the author of Chump Change and Housebroken: Confessions of a Stay-at-Home Dad. Damage Control, the book, was released in March.

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