Stakes too high to gamble on mate’s honesty

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This article was published 26/11/2025 (300 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: My boyfriend says he’s a great gambler — so skilled he makes money rather than losing it most of the time. At least that’s what he reports to me when he calls me at the end of a night out with his friends.

A suspicious girlfriend of mine is urging me to tell him to come to my place and show me the money after he wins. She says she doesn’t believe any gamblers tell the whole truth about what they lose, and she should know, because she used to be married to one.

I don’t care so much because he and I don’t share our money and I’ve always handled my own finances. I really like to pay my own way. The thing is, he’s been hinting he wants to marry me.

Why should I be concerned over what my friend is hinting at? She knows my guy from way back, as they went to university together, but she’s acting like I shouldn’t trust him further than I can throw him. She’s trying to spoil this romance for me.

Do you think I should I be worried about him, or is she just jealous?

— Nervous Now, North Kildonan

Dear Nervous: Buttonhole this friend and make her confess what she’s not coming right out and plainly telling you about what she knows about your guy. Demand detailed examples of what’s going on with him — and you might get them.

In the best scenario, she truly won’t know anything else but has just heard some gossip, but really try to get some details so you can try to clear this up before proceeding with him.

If you do want to tie the knot, you might find you’re not so comfortable with a guy who gambles a lot of money, even if he doesn’t touch yours. For instance, you might be looking at buying a house together, find a good one and suddenly discover he no longer has the chunk of down payment to match yours anymore, which he claimed he had saved, because he may just have lost a whack of it in a game of chance or on a horse he was “investing in.”

You would never know what kind of nest egg he really has. He would have a secret life.

Some gamblers also get into serious trouble with people in the illegal gambling world. Some can be rough people, who don’t take kindly to those who don’t pay up.

Dear Miss Lonelyhearts: I ran into my half-crazy old girlfriend while at a mall the other day. She looked so happy and healthy that I stupidly complimented her.

I couldn’t believe what she said back, quite loudly so loud other people could hear: “I was allergic to you and your crazy moods. You dragged me down every day. I want to thank you for breaking up with me. The best thing I ever did was getting over you.”

It felt like she had slapped me across the face, like she used to do when we were together. What should I do now? I feel so hurt and upset — like I did every day at the end of our relationship.

— ‘Slap’ from the Past, Steinbach

Dear ‘Slap’ from the Past: She’s not your worry anymore, but she’s certainly managed to upset you once again.

When someone seems “off,” it’s a good idea to steer away from them and not engage when they confront you, even if they have a big smile on their face.

It’s important to put physical distance between you and this woman who used to be in your life. That’s even if it means turning on your heel and walking in another direction when you see her. That can be harder when you live in a smaller community.

Just don’t let the charm they may employ while talking to you fool you into thinking they’re different now. Risk being rude, make any excuse and walk away quickly so they don’t follow.

Also, block their number on your phone and take them off your social media.

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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