Mom’s criminal past a lot to unpack by yourself

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This article was published 20/05/2025 (490 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I thought I knew my single mother’s history — until I found out she actually went to jail for a short time many years ago. Nobody ever mentioned this fact to me — her daughter and only child — until we were sitting around at a barbecue at the lake recently.

It was getting late, and two of my uncles had been drinking a lot. The topic of jail suddenly came up. My mom, who never drinks a drop, started gesturing wildly at her brothers and hissing at them to shut up, but it was too late. She finally grabbed my arm to hustle me quickly out to our truck.

After a few miles of driving quickly, she had tears streaming down her cheeks. I just waited. Then she started telling me what went down when she was part of a gang a long time ago — and went to jail.

Now I admire her for telling me the truth, but I felt sick to my stomach then and threw up. We didn’t speak all the rest of the way home.

The next day I got up the nerve to ask her why she did the crime that got her sent to jail. She said, “Because we were drinking and doing other stuff and it seemed exciting until somebody got hurt.“

I still don’t know the whole story. She wasn’t ready to tell me more.

My question is how do I make sense of the fact my mother is so good to me and everybody else, and yet she did illegal things to a degree that got her sent her to jail? I just don’t get it.

— Head is Spinning, Winnipeg

Dear Head Spinning: Some people “fall down a hole“ for a portion of their lives, particularly after they get in with a bad crowd and suddenly start doing illegal or dangerous things they would never have dreamed of doing on their own.

If a newbie in a gang is already into drinking or drugs, they’re even more usable for a group caper because they need money to support their habit. Your mom may have been lonely and desperate for friends and found herself drawn in by the friendly overtures of a gang, who saw how easily she could be manipulated.

As well as talking to your mother, it’s time to get personal help from a counsellor who has experience helping people who have been in serious trouble with the law and done jail time.

A social worker could help you find a good person to help you learn about how things work and get through this uncomfortable time with your mom.

Dear Miss Lonelyhearts: We have new neighbours at the lake (they just bought two doors down from us) and my second wife hasn’t met them yet.

I know the man from competing for work projects with me, and he gets around. How do you warn your wife, or do you say nothing and hope it resolves itself? I know this guy. He will always make a move if it’s female and it’s breathing.

— Neighbour Problem, Whiteshell

Dear Neighbour Problem: When you do run into this couple, say hello and engage them in a short, boring conversation and a “Gotta go!” You want your new wife to yawn when she sees this old snake, so you can have a peaceful co-existence with these neighbours at the lake. That will mean refusing all invitations from them with well-rehearsed excuses.

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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