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DEAR MISS LONELYHEARTS: I’m in my 30s, but feel older because I spent some time in jail during my youth. I don’t know how or when I should tell my new guy. I was addicted and did all the bad things people have to do to get money to buy drugs. But I finally cleaned up my life with help, moved to Manitoba and started a new life.

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Opinion

Hey there, time traveller!
This article was published 22/10/2025 (271 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I’m in my 30s, but feel older because I spent some time in jail during my youth. I don’t know how or when I should tell my new guy. I was addicted and did all the bad things people have to do to get money to buy drugs. But I finally cleaned up my life with help, moved to Manitoba and started a new life.

Last night, my new guy said to me, “There’s a lot about you I don’t know, and a lot about me you don’t know. Are you ready to talk about some real things? Should we start getting to know about our pasts?”

I gave him my worn-out old line: “The past is the past. Let’s leave it that way. I like it the way it is with us — fun, pretending we’re younger, and starting new and fresh with each other.”

Then something got into me. I added the tell-tale line, “I don’t want to know about your past girlfriends, or the trouble you got into. I had enough of my own.”

He took my hands in his, and said, “I met someone who used to know you, and he told me some things I was a little shocked about, but I’ve worked through it, and now I’m ready to trade my secrets with you.”

I asked if that was true and he said it was. He even knew about my time in jail. I started to cry but he took my face in his hands, and told me that he and an ex-girlfriend had a child together, but who he can’t see.

I asked what terrible thing he did so he couldn’t see his own kid, and he said he got her pregnant, although she was married.

“The baby is darker-skinned and looks just like me. Her husband is white, and so is she. Her husband chose to stick with her because of the child. I have only seen pictures of the boy she’s secretly sent me,” he said.

Then he showed me a photo and we both shed tears and held each other for a long time.

How do we start over after that difficult exchange? This man I think I love, says he does not want to go to therapy, and he’s digging in his heels. We have no money for it anyway. But what else can we do?

— At a Loss, East Kildonan

Dear At a Loss: Here’s my own exercise for you and your man that could open up a sharing of feelings that will help you dig out of this complicated situation.

First, get two small markers and big pieces of paper and fold them into halves. On the first page you both write, “Before I met you I was feeling…” Then you go first. Choose words for your emotions such as sad, misunderstood, lost, worthless, angry, scared, trapped and embarrassed.

Then your man might write, “Before I met you I felt lonely, empty, aching for my child, guilty, worried my boy will think I rejected him, afraid he is teased and worried the white dad will take it out on the boy for his mother’s affair.”

Here’s the happy part. On the second pieces of paper, you write words starting with, “Now that I’ve met you, I feel…” It may be things such as hopeful, excited or accepted. You’re welcome to say anything, such as, “You’re my new love and my deepest friend.” Let it sink in for a few minutes.

By the end of this revealing mini-therapy you may both feel more like laughing, hugging, telling silly jokes, planning dates and little road trips, and telling each other your other secrets and regrets. Together you may start to feel, “Now everything is revealed, there is hope for us.”

Want to go further? On another night, exchange this affirming quote, saying back and forth to each other: “I’m relieved we are opening up to each other, laughing more, not expecting perfection, loving exactly who we are and accepting everything.”

Dear Miss Lonelyhearts: My daughter is way smarter than both her parents combined. She, in Grade 9, is already investigating universities (in Grade 9) because she wants to go on historical digs all over the world. Last week, she asked her dad and me if we had an education fund going.

When we said yes, she said that was good because we were going to need it. She said she was going to also get a part-time job to start kicking in money, too. This week she actually came home with one. She’s working at her best friend’s parents’ store on weekends.

I asked her today if she ever has just plain fun, and she said, “Every day, on my computer.” Can that be good for her?

— Worried Parents, East Fort Garry

Dear Worried: Kids have a great time on the computer — real fun. To balance that out, they need physical exercise and getting outdoors. Just try to help make sure she has that in her life by using fun trips away from the computer with a buddy — like to a skating pond, tobogganing hill or swimming pool.

You may need to make it more fun than the usual fare to entice your computer brainiac and her pals from their chairs for a few hours, but then you can stop feeling guilty about your modern kid.

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

Maureen Scurfield
Advice columnist

Maureen Scurfield writes the Miss Lonelyhearts advice column.

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