No need for scheming to express your interest

Hey there, time traveller!
This article was published 25/07/2025 (463 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I recently met a great speaker at a small-business conference who is newly divorced. He was not embarrassed to talk openly about himself after the speech. He isn’t overly handsome, but he has a friendly face and a great sense of humour.

I was at the front of the room where everybody seemed to be competing to get close to him afterwards and hear his funny off-the-cuff comments. I muscled right in and tried to impress him.

Even better, I managed to get a seat right beside him in the hotel bar after his presentation. I’m not shy, so I fished for details about his personal life — and got them. I told him I was single and gave him my business card. He seemed happy to give me his.

Then I had a bright idea. I suggested he should be a speaker at one of the small conferences I organize in Winnipeg. He looked at me a little suspiciously.

I said to myself on the drive home, “Am I looking for trouble with this guy?” Maybe I am. What do you think about all this?

— Can’t Stop Thinking About Him, Tuxedo

Dear Can’t Stop: Why not just be honest with this guy, so he isn’t suspicious? You have his contact info, so call him up and tell him you really enjoyed his company and would like to see him again.

Honesty will save you a lot of time and allow you to be natural and not come off as a schemer.

Tell him you would like to have dinner with him. What can it hurt?

Dear Miss Lonelyhearts: My husband is a sad sack these days and the kids are sulking. I’m also very frustrated because it’s so smoky at our rental cottage on Lake Winnipeg. We’re driving in and out of the city all the time because of the wildfire smoke.

We won’t be spending enough time there to justify paying for the whole summer rental period. But the cabin owner certainly is not offering us any of our money back. He said he couldn’t even rent all his cabins this summer — the first time ever.

I’ve been taking my kids to activity centres and museums when we’re in the city, but that’s become boring for them. Yesterday, my oldest boy said we should just watch TV, save our money and hopefully we can go to the lake again in August.

He didn’t sound hopeful. How sad is that? My heart sank.

I’m a teacher and have July and August off to be with my family and I had hoped to give them a summer to remember. How can I make the last part of this summer better for the kids?

— Sad Mom, St. James

Dear Sad Mom: Refuse to take on the frustration and depression from people around you, so you’ll have the energy to find new things to do and salvage the summer.

Take the time now to make a list of indoor events and places to go with your family for the few weeks left of summer. (The Free Press published a two-part list this month: wfp.to/summerlist)

Everybody likes swimming, so start by checking out pool schedules online. Air quality at the city’s indoor pools is good, but if you want to be sure to get your kids in to swim, you may have to line up before opening time.

You could also consider throwing a party for your kids’ friends. If you have enough money to hire a children’s entertainer — a magician or musician — it will be a guaranteed success. Invite cousins and neighbourhood kids over for the party and serve up hot dogs and ice cream. Don’t forget the goofy hats and party favours.

The party could be the highlight of the summer for your kids.

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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