Dear Miss Lonelyhearts: I’m 29. My boyfriend is younger than I am, and more serious. I was married before, so I’m wary.


Dear Miss Lonelyhearts: I’m 29. My boyfriend is younger than I am, and more serious. I was married before, so I’m wary.

He is an only child and is excited about the prospect of love, marriage and a baby carriage. He’s so anxious to get moving, but I’m dragging my feet.

Last night he asked me a serious question. He wants to know "if I’m considering all that with him one day," or if I’m done with marriage and kids after my first husband.

I just don’t know! I was fooled before. I was married to a sweet and romantic young man, who turned out to be violent.

How do I know this man won’t turn out the same once I’ve signed the marriage certificate? — Dragging My Feet, West End

Dear Dragging: You could make the same mistake by going too fast.

This guy is anxious to push his own agenda. He’s not thinking about you — he wants you to take the fast train with him.

Look, you have serious doubts about him or you wouldn’t be writing. Listen to the intuition that’s telling you to step on the brakes and get off this locomotive.


Dear Miss Lonelyhearts: I’m in my late 60s and feeling very lonely. My wife has been gone for just over five years, and while I have a wonderful family, my own home life is spooky quiet. But I feel like if I started dating again, it’d hurt my two grown "boys" who have wives and children of their own now.

You know how "adult children" can be; even if they’re in their 30s, they still act like they did as kids.

Father’s Day is upon us again, and they used to like to get together — Grandmom, Grandad, themselves, their mates and their tiny kids. This time, because of COVID, my two sons and I will meet in my backyard for a few beers.

How could I approach the subject with them in a way that wouldn’t hurt their feelings? It has been quite some time now since their mother passed. I want to get on with my life! — Lonely Too Long, Transcona

Dear Lonely Too Long: Your kids didn’t ask permission to start dating, did they? You don’t need to, either. It’s an awkward question to ask grown kids who have lost their mother if it’s OK to start dating to try to replace her.

So, people in your position should just subtly start looking for a new relationship and hope the family will like the new lady you pick, when you bring her around.

That is something you should do only if things are becoming serious — to see how she reacts with your children and grandchildren. They only need to like her — not love her — in the beginning, to pass muster.

Who knows? Your sons may be happy you have found someone. The idea is to expand your circle of family to include a happy new mate — not to marry a woman who doesn’t fit in with the family and keeps you away from them.

The trick is to introduce her part way through a family gathering, when things are already cooking, and she doesn’t feel she’s on display.

For now, hunt in private and date once you’ve had both COVID vaccinations and they’ve had time to kick in. Dating is scary enough without fear of the coronavirus.

And yes, you and your potential partner are certainly both within your rights to ask for proof.

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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