Don’t forfeit sure-thing date with your crush

Maureen Scurfield Miss Lonelyhearts
By: Maureen Scurfield Posted:

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DEAR MISS LONELYHEARTS: I have a bad problem and I’m ashamed to admit it because it was all my fault. I introduced my best friend to a man I wanted myself since I thought he wasn’t interested in me. He was gracious and asked her out for dinner and they went — and I stayed home and pouted.

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Opinion

Hey there, time traveller!
This article was published 16/01/2026 (201 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I have a bad problem and I’m ashamed to admit it because it was all my fault. I introduced my best friend to a man I wanted myself since I thought he wasn’t interested in me. He was gracious and asked her out for dinner and they went — and I stayed home and pouted.

My friend phoned the next day and told me the guy spent the whole night talking about me and he asked her why I never respond to him and his jokes. What? I do think he’s funny, but I’m not a loud laugher.

I’m a shy person, so I couldn’t possibly pick up the phone and call him and tell him I would love to go out with him. I just can’t.

What can I do? I also know I shouldn’t let this nice guy go.

— Kicking Myself Hard, Osborne Village

Dear Kicking: Your friend told you everything this man said about you because she is not interested in him herself. If you give her permission, she would probably tell him straight up she spoke with you and that you would be very happy if he called you and asked you out.

What’s the worst that can happen? Maybe he doesn’t call right away because he’s shy. Big deal. Then you could hang out with this helpful girlfriend and call him (with her right beside you) to ask him to meet you for lunch. It won’t be that hard because you now know he clearly wants to date you, so success is pretty much guaranteed. In fact, he’ll probably be delighted to hear your voice.

He doesn’t have to know you were hanging on to your mutual friend’s hand to give you the courage to call him — until you’ve been dating him for a while. Then it will be funny for both of you.

Dear Miss Lonelyhearts: I usually hide out until January is over because it’s so cold, but this year I have an overseas student living with my family. We are trying our best to show her Canada is not so bad in the winter and have taken her skating and cross-country skiing. She hated it. Help us. What can we try now to help her get used to our winter?

— Pulling Our Hair Out, Westwood

Dear Pulling: Forget trying to immerse your foreign student in the cold. Instead, teach her about movie nights and hot chocolate with marshmallows and fluffy blankets and heating pads. Then there are the board games she might not know yet, and lots of card games to play.

She might also enjoy going to indoor concerts and plays and all the live entertainment Canadians enjoy while enduring the coldest part of winter and craving escape.

She doesn’t have to love this season — not all of us do — she just needs to learn how to adapt in warm ways that end up suiting her.

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

Maureen Scurfield
Advice columnist

Maureen Scurfield writes the Miss Lonelyhearts advice column.

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Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.

Maureen Scurfield

Maureen Scurfield
Advice columnist

Maureen Scurfield writes the Miss Lonelyhearts advice column.

   Read full biography

Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.

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