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This article was published 27/08/2025 (418 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I retired and finally started having a real affair with a man I’d always desired and flirted with while we worked together.

Years ago, he was a real scamp at the pub when we went for after-work drinks. I was the “saucy brat” type, so we really clicked. There was lots of playful name-calling and heated discussions going on between us!

We always went out to the bar with other people — a kind of unspoken rule. We both seemed to know we were in danger of going too far if we didn’t, especially after I got divorced from my husband.

So now, here we are in 2025 actually seeing each other, and I do mean all of each other! People from work must guess at how far things have gone.

I wonder if his wife knows — but if so, it doesn’t seem enough for him to stop. In fact, I want us to be together openly, but he doesn’t mention if he’ll ever leave his wife. What do you think? I can’t discuss this with people who know us both, or the dam will break and I’ll cry buckets.

What should I do about this affair of ours? I don’t think he’ll ever leave his wife, now that he has everything he wants. Should I threaten ending things?

— Feeling Sick, downtown Winnipeg

Dear Feeling Sick: Your affair was at its best when you two were forever chasing each other at work and the bar, but never acting on it or seeming to need any kind of commitment.

Do you wonder if he’d actually like to be free to marry you, or does it hurt too much to ponder?

It seems like your relationship is a tower of blocks you have to carefully balance, so it doesn’t topple.

So, allow yourself to project ahead in time and imagine different ways it could end up, if you finally pushed a little harder.

Work through this important exercise with a relationship counsellor or a psychologist. That could help you finally decide what you want to do at this juncture.

If you’re feeling extra-courageous, you could finally ask this man what he envisions if there’s a future for you two. He might love you romantically but not want to give up a wife he loves in other ways that are important to him.

Dear Miss Lonelyhearts: I ran into a ghost the other day! I had heard this old girlfriend of mine from high school had been deathly ill, and I’d just imagined she’d be gone by now — but then she got on the elevator with me in a big building, and my face turned every shade of red. I couldn’t say what I was thinking which was, “I thought you’d died.”

Nope! She was very much alive and insisted on taking me for a boring drink to explain what a medical wonder she turned out to be! Then she pressed her new phone number into my hand, but I didn’t give her mine in return.

Now what? I don’t want to call her, but I don’t want to be rude.

— Had Enough, St. James

Dear Had Enough: You don’t owe any old lovers a phone call, even if they foist their current contact info on you. It’s an offer to be social with you, but not a duty for you to respond.

It’d be worse if you called her just to be polite and she got excited thinking you were going to ask her for a date — and instead you only mumble pleasantries and comment on the weather. How annoying!

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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