Food for thought when it comes to dating game

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This article was published 30/12/2025 (250 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I’m a divorced woman who is making a New Year’s resolution to ask out guys I want to get to know better. So far, I’ve made a list of three.

It takes a lot of courage. I’m not a young woman, and I’m in sales. The only thing I can’t seem to sell is myself — and I’m friendly and nice-looking. Should I ask them out all at once, like I would if I were blitzing a sale, or should I try one and if that doesn’t work, try another?

— Blitzer, St. James

Dear Blitzer: The blitz makes more sense for you because dating one at a time could wear you out emotionally, after even one or two rejections.

Food dates you pay for, as in “Want to join me for a pizza — my treat?” are likely to win you more accepting replies than “Want to go to a movie with me?” because you have to sit in the dark for the first 90 minutes of the date.

So, if movies are your thing, it’s smart to treat your date to a pizza first, so you can chat and get comfortable with each other before the lights go down and you’re sitting there having to be quiet for two hours.

Of course, after lights go back on, there’s the movie to talk about — and that’s easy because you two just shared the experience.

Dear Miss Lonelyhearts: My boyfriend and I were supposed to be the perfect match because we were so much alike that people at school said we were like twins. Our parents were all for the relationship because they thought it was fun and amusing that we could finish each other’s sentences.

Don’t they realize how boring that is? Now, how do you break up with somebody whose only fault is that they are just like you? He’s not saying anything critical about me, but I can feel the boredom growing between us.

— Difficult Situation, North Kildonan

Dear Difficult situation: You tell the boyfriend, your parents and the other people who think you’re so cute together that it’s boring to be so alike. Your lives are too precious to be used for entertainment by others.

Tell them you’ve discovered it’s the differences that make people unique to one another and you two are starved for more of those differences. Then just break up, and let everybody find another couple they think is cute and get their amusement from them.

Dear Miss Lonelyhearts: A man came to the door looking for my mother and I went to the kitchen to get her. When we came back, he looked at her and said, “I just wanted to see that you’re alright.”

Mom told him that she was fine and not to worry about her, then he turned quickly and left.

I asked my mom who he was, and she said it was an old boyfriend who broke her heart. “I believe he’s with a man now and that’s what really needed to happen,” she said. I asked her if she would tell me more about it, and she said she wasn’t ready to talk. Now what?

— Upset Daughter, Crescentwood

Dear Daughter: Some old heartaches are so deep, parents can’t talk about them. Even though they’ve recovered to some degree and have a new love, they can’t dig up the bad situation and discuss it. You just have to accept that. Not every heartache can be shared with people who love us, although it was sweet of you to ask.

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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