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This article was published 14/03/2025 (584 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I spotted my old girlfriend recently at Canadian Tire standing with a couple of little kids. I looked left and right — no husband around. I was in a crazy mood, so I gave her a little wolf-whistle just like she used to do to me in high school. Bold thing she has always been, she put her fingers in her mouth and whistled right back. It used to be our thing. I felt a rush of excitement and old feelings.

Her three kids were looking up at her like they couldn’t believe their eyes and ears at what Mommy just did in the store.

I saw my opportunity. I galloped over and said a big, “Hello everybody,” and then asked to be introduced to the little gang and met them all.

After a chat with them, I asked their mom where her husband was and the little girl with her high voice announced, “Mommy and daddy got de-borced.”

I looked at their mom, and said in a quiet voice, “That’s interesting to hear.“

My ex broke into a smile, and that was a new beginning — I hope.

Since then, we’ve been chatting here and there, and sometimes she actually phones me first. She usually lets her little girl, who loves talking on the “big-girl phone,” say hello and talk to me for a few minutes. I don’t have kids, so I get a big kick out of it.

I would really like to ask her out and try to take things further than a friendship. I was too independent when we were younger and she couldn’t settle me down.

What would be a good time to ask her out? I’m ready, but I’m not sure she is. I know she likes the way I’ve built up my body because she’s mentioned it already. I’d like to give her a closer look at it.

— I’m Back. St. Vital

Dear Back: So, what’s the full story of why you two broke up? Plus, is her husband now a permanent thing of the past? There’s no point in digging in again emotionally if your old sweetheart is still hoping he will come back.

However, if he’s truly a thing of the past, then great. Maybe you can become the terrific guy who makes her forget about him for good. That might mean taking her out to dinners, concerts, movies and sporting events she would enjoy, and, of course, a deeper intimacy between you two.

Ask her on the phone some night what she’d like to do to have fun with you and to rediscover each other, but be sure you have remedied any issues that drove you apart before. If it’s not fixed, you’ll just be headed for emotional crash No. 2, and who needs that?

P.S.: Don’t make the mistake of trying to be the kids’ second daddy — at least not until you and their mom get serious. Just be their kind and fun friend to start with, as they’ve likely had enough instability in their young lives.

Dear Miss Lonelyhearts: I’m an older guy, and, like some well-to-do seniors who’ve written you, I also help my female friends go on holidays each year. I pay for their plane tickets and they pay for the shared lodgings. We go as equals, like buddies.

We eat together a lot and go for drinks at bars where Canadians like to go — we have lots of fun and we’re never lonely.

I let them know I’m not looking for sex with them, just friendship and companions for meals, clubs, sightseeing and so on. I don’t sleep with any of them, but sometimes I meet a lady from another crowd and I might get lucky with her.

This year, however, I have a problem developing. One of the women who accompanied me recently has declared hidden feelings for me, and says she finds me good-looking (and mostly wants her next trip completely free, I think).

I don’t kid myself she’s crazy about me, although she might be in love with my money. She was always the first to argue over things with me. What do you think?

— Fear a Schemer, South Winnipeg

Dear Fear a Schemer: Trust your instincts. Tell this woman you don’t share her feelings beyond enjoying a friendship. Also tell her it’s time to give some other people a chance to go with you.

She will not be happy, as her plan may have just backfired. Maybe that’s just as well as you two have already worn out the “beach buddies” situation by this point.

Please send your questions 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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