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This article was published 08/09/2025 (418 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I love people’s second marriages, where two people who first made mediocre choices finally marry their way-back loves. I really need to do the same thing. There’s nothing wrong with my wife, except for the fact she packed up and left me. Apparently I am a colossal bore.

What a wake-up call. She had never really been the one I truly desired either. Truth be told, I actually preferred her sister.

Then I got another happy shock when I learned an exciting married woman (there had been some serious mutual flirting between us in the past) just pulled herself free from her soul-sucking husband.

Now I want to show up at her place some night in a hot convertible, honking my horn and yelling, “Hey, babe — come on out and jump in. Let me take you on a wild ride.”

What do you think — am I too old to do something like this? Sometimes I feel drunk on possibilities, but I need some good advice as I set out on my new adventure.

— Time to Follow Heart, rural Manitoba

Dear Time to Follow: You are just the right age to yell whatever makes you feel good again. To show this woman the “wild man” in you, first take her out on a fun date — some surprise she would really enjoy that you’ve planned for her.

If things go well, on the next date, get caught up on both your lives, sharing stories parked under the moon somewhere. You’ll soon find out if she thinks you would still be a fun match.

It could be great start to something, or she could be a bomb, and the same for you from her perspective. It depends on how you’re feeling coming out of your respective marriages and if the two of you are compatible.

So don’t get ahead of yourself here — what you need is a mix of maturity and youthful spirit, and communicate your real feelings and opinions on life. (And make sure to avoid criticism of your exes.)

Just because the two of you are out of unhappy marriages doesn’t mean a magical relationship is just going fire up — it takes some real work and honest communication.

Dear Miss Lonelyhearts: I could not be more shocked. My recent ex (a female) is seeing a number of people now, and only one of them is a monogamous guy.

The two others are with her in what I can only describe as a novel sort of three-way to “try out new things,” as she explained to me.

Why couldn’t she have done this with me? I’m an open-minded, good-looking guy. I was always up to experiment with her and someone else, but she curled her lip at that.

I was so willing — maybe a bit too much. What does it take?

— Puzzled, West Kildonan

Dear Puzzled: It takes a medium-close couple to experiment together — a duo who think the same way and have similar tastes in new people, and in the sexual adventures they would like to explore. It could be that you were a bit too eager, or maybe she just didn’t think your personality was good fit for this sort of thing.

It’s also something that may not work for a close, committed couple looking forward to one day being in a tight one-on-one relationship with a view to starting a family together.

In other words, you need playmates who want to remain playmates. Jealousy is the enemy in these multi-element couplings, so you don’t want to get too intimately entwined with playmates who could provoke those hurtful feelings.

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.

Maureen Scurfield
Advice columnist

Maureen Scurfield writes the Miss Lonelyhearts advice column.

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