Dear Miss Lonelyhearts: I was shopping for groceries, wearing my mask, when this long-haired guy winked at me over his black bandana from the neighbouring checkout.


Dear Miss Lonelyhearts: I was shopping for groceries, wearing my mask, when this long-haired guy winked at me over his black bandana from the neighbouring checkout.

What a sexy bandito — and he was kind of familiar! It took me a few minutes to realize it was my immediate supervisor from my first real job. I knew he liked me then, but it would have been wrong to flirt with me at that place. But I’m five years gone from there!

He was waiting for me outside — no surprise! He’d never lacked nerve. We chatted away, like we’d never been apart. Then a woman pulled up, popped the trunk and he threw in the grocery bags. She looked old enough to be his mother. Maybe she was… oh please, God!

I want to see him again in the worst way (and the best way!) but it wouldn’t be cool for him, a former boss, to call me. Should I call him at work?

— Dying to Talk More, Southdale

Dear Dying: Obviously, you don’t lack nerve either! So why not call him? The first question out of your mouth should be: "Was that your mom in the car at the store?" Get that out of the way, before proceeding even one step further.

He may shop with mom or an aunt — or he may have an older wife. If he says "my wife" then you’ll want to be brief, as in, "Nice to have seen you again. All the best!"

No need to keep on with a lame conversation. He knows why you called — the same reason he winked!


Dear Miss Lonelyhearts: I’d been dating one of the nicest women around, but there’s a painful problem. She asked me to move in with her, and I eagerly accepted. She has my heart. She also has a teenage son who lives with her part-time.

I have no children of my own, so suddenly having a built-in family warmed my heart. To have a stepson to do normal guy things with, was so much fun. We bonded quickly, and he seemed much happier overall.

Then things started to change. My stepson suddenly became very cold towards me when he came over. On my birthday weekend he barely looked at me. I tried to have a private talk with him, and he yelled, "You’re not my father, so stop trying to be!"

I left the room, feeling confused and hurt, mostly for him. I have my suspicions why things changed. I’m not his father, but I do love him and want nothing but the best for him.

His mom tells me his father has recently become jealous of the relationship between her son and me. The boy’s father has also been emotionally and physically abusive towards him in the past, but mainly ignores him these days.

I’m at a loss for what to do. My stepson suddenly won’t talk to me, or even look at me. I also understand the teenage years are difficult. I love my girlfriend and her son, but I’m finding it difficult and feel like I’m always walking on eggshells. What to do?

— Confused Stepfather, Winnipeg

Dear Confused: You are not the boy’s stepfather, but because you use that term freely, he may have picked it up and bio-dad is angry and jealous. The fact you love the boy like a real dad may have come through.

You have no idea how much that man quizzes his son about you and the activities you do together as a family.

So, it’s time to be relaxed and casual. Don’t say the words "love" or "stepson" around the boy. One day soon you might say, "Through your mom I’m starting to understand how difficult it is for you to have two dad figures in your life, so I want you to know I’m stepping back to be your friend — but only when you want that attention from me."

Then you must step back without showing too much hurt, because the kid is carrying enough guilt around already. Let him slowly settle into an easy friendship with you.

This boy is not old or savvy enough to be able to walk two lines at once. He needs to know what to keep to himself to please his father and still enjoy a few activities with you.

Try to stay pleasant and relaxed around the house, until a kind of equilibrium is reached. You think he doesn’t know how much you care? He does, and he may acknowledge it later, when he feels freer.


Dear Miss Lonelyhearts: My long-term girlfriend of eight years is well-known to our set of friends. They know she likes to get super-drunk once or twice a summer, dance and sing stupid songs, jump off the dock without her bikini top, and generally play the fool.

I don’t mind her annual blow-outs, as they take down her considerable work stress, and she really relaxes the rest of the holiday.

This year is not the same because of COVID, so the drunken parties are not happening. We see our best friends there, and that’s about it — my bright idea. Little did I know the storm it started brewing.

Yesterday, my wife announced it was just too hot and she wasn’t having any fun with me, so she was going home! She threw her clothes in a bag and drove off in her little convertible. I was mad and stayed at the cabin with the dog.

We have another two weeks of holidays. On the phone she says she’s sick of me and my stupid rules, and not coming back to the lake. So, it wasn’t about the heat, but about my curtailing her wild partying with the old crowd.

— Party Pooper, Lake Winnipeg

Dear Party Pooper: Since you care, drive home for an overnight and try to make up. Promise you won’t interfere in her party animal performances next summer, if everything’s safe.

Then drive back to the lake if you have a few days left — with or without her. Whatever you do, don’t let her hissy fit wreck your whole summer holiday at the lake. Partners should not be allowed to get away with dramatic tactics like this.

Please send your questions and comments to 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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