DEAR MISS LONELYHEARTS: I must confess I picked up a man in the grocery store recently, and took him for a walk. He was a guy who recognized me from high school, when I was considered a red-headed hottie. He said he heard my laugh, and knew for sure it was me.

We were both wearing masks, but I recognized him (dark brown eyes, black curly hair) when he introduced himself outside the store. We were standing there feeling awkward, so I asked him if he’d like to go for a walk with me. We walked (distanced) and talked wearing masks all the way. He confessed he’d always had a crush on me, but I was always going steady with one guy or another.

Now we’ve been on two long walks and I really want to invite him to my place for dinner and whatever, where I live alone since my last husband died. He’s divorced, and we’re both in our early 50s. More importantly, he still works at his office with other people.

I’m afraid of contracting COVID myself, but even more because I have grandchildren I’d love to babysit again after lockdown rules ease. I told my daughter about this new man I’m attracted to, and want to start dating. Her eyes flew open, and all she said was, "Please say you don’t mean that, Mom."

She finally calmed down and said it was all right if I started dating him, but only if he and I went and took COVID tests, as he could be "asymptomatic." And she also asked me, "Does he wear a mask at work?" She doesn’t trust my judgement, or his!

This seems really pushy and unnecessary to me. What do you think?

— Upset Grandmother, St. James


Dear Upset: Your daughter sounds normally protective and unafraid of annoying you. Why is that?

He may be a sweetheart, but you have no idea who’s included in this man’s circle at work or elsewhere, even if he claims it’s nobody. Bottom line: If you want to start dating somebody new, both of you should get tests. That’s the least you can do. Your daughter is right, and your faulty judgement is not to be trusted on this issue, no matter how sweet this guy is.


Dear Miss Lonelyhearts: I broke up with my girlfriend because she was too clingy, and now she keeps phoning and phoning, saying she’ll change. I don’t care what this girl promises. Her constant calling has never even given me a chance to miss her. She was a nice girl — very pretty and smart — but a spoiled only child. When she doesn’t get her way, it turns out she’s relentless!

I was on good terms with her mother. Should I call her, and ask her to tell her daughter to leave me alone? Please don’t suggest blocking her, as that seems heartless.

— Nice Guy, south Winnipeg


Dear Nice Guy: You can be too much of a nice guy, and this is such a case. You could call your ex’s mom, but she might be on her daughter’s side and want you back together — and try to persuade you to give it another try. It’s time to tell this relentless girl you will have to block her if she keeps calling you.

Tell her clearly it’s over for good and that no apology is going to get you two back together. You’ll have to be cool and firm. You have had it, and her calls are starting to feel like harassment. Consider ending your little speech with: "Listen, this is the last time I’m going to ask you to leave me alone, before blocking you."

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.

Miss Lonelyhearts

Miss Lonelyhearts
Advice Columnist

Each year, the Free Press publishes more than 1,000 letters to Miss Lonelyhearts and her responses to the life and relationship questions that come her way.

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