Be honest with birthday boy about trust issue

Miss Lonelyhearts
By: Maureen Scurfield Posted: 2:00 AM CDT Monday, Oct. 6, 2025

DEAR MISS LONELYHEARTS: My marriage to a controlling older man didn’t last a year. I was young — in my 20s — when I got divorced. It was a bad mistake. I married him partly to get away from my wealthy, know-it-all parents.

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Hey there, time traveller!
This article was published 06/10/2025 (303 days ago), so information in it may no longer be current.

But after the divorce, I was scared to date another man. I dropped out of the whole scene. But recently — to celebrate my birthday — my girlfriends took me to dinner and the bar. That night I met a great guy about my age and we danced all night long.

His eyes and crazy sense of humour were oddly familiar. We didn’t trade last names until the end of the night — and then it was a shock. One of my friends had the same last name — it turns out he was the cousin of one of my girlfriends out for my birthday. It was a just big setup.

She confessed she pulled the stunt as a present. It could have been a bad thing, but it wasn’t. I really liked him. But now I have a timing problem. I still lack trust in men, but I think I recognize a winner in this woman’s cousin and I am so interested in seeing him again.

I still think I probably need counselling about my trust issues though. Do you think it would be a mistake to start seeing this guy before I’ve worked out this problem, or will I lose him?

— Scaredy Cat, St. James

Dear Scaredy Cat: Some guys would congratulate you for taking care of your trust problem first. Others might thank you for the confession and quietly slip away. Still others would ask for a rain check because they’re interested, but don’t want to be part of a heavy conversation and your therapy process.

So, consider telling this attractive person you really like him and you’ll be sure to give him a call for a date once your trust in men has clicked back in. Just don’t wait too long.

Dear Miss Lonelyhearts: I gave my older boyfriend a really expensive watch with some engraving on it for his birthday in September. I couldn’t be more shocked now. He has just broken up with me to start seeing another woman, who is older than me, by a lot.

I am so angry and upset. I spent a lot of money on that watch — over $1,000. So, I demanded it back. I told him on the phone he owed it to me.

He asked if I was kidding. “That was a gift from you and it has an engraved message with my name on it. People don’t demand birthday gifts back if they have any class, which you obviously don’t,” he said.

I replied by asking him to pay me back the money I paid for it and gave him the actual number. He hung up on me and I can’t get through anymore. What chance do I have? I really want my money back.

— Gone Forever? East Kildonan

Dear Lost Forever: That expensive watch was definitely a gift from you to this man for his birthday, and you openly admit to that. You can’t demand that watch back or ask for the money spent and expect anything — unless the receiver feels sorry for you. You made sure he wouldn’t.

Your ex probably can’t sell the watch himself for much with the personal engraving on it unless he gets a jeweller to somehow cover it up. Why would he go to all that trouble after the way things ended with you?

So, just chalk up your expensive-gift mistake to experience. Also, talk to a therapist about trying to secure love with an expensive gift. Did this kind of thing happen in your own family life? It’s time to put an end to this kind of thinking in your own young life.

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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