Kudos for listening, but it’s time you share more

Hey there, time traveller!
This article was published 10/06/2025 (465 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: Unlike a lot of guys, I want to get married again — like, right now. I’ve been married twice, and I don’t mind admitting I’m lonely. I’m sick of dating again at 44. Plus, I’m a guy who really wants kids while I’m still strong and fit.

Sex meant everything to me in my 20s. It turned out “love” also wasn’t too hard to find, if I asked enough questions about what a woman needed from a guy. Then they felt seen “on the inside,” or so they said.

I often found women really need a free adviser like me, who actually listens. Some women that I’ve known thought I was just playing with them because I’d go for drinks, and listen to their problems dealing with another guy, no problem.

I saw myself as the guy who’d love them, accept them and maybe they’d take me into their heart, but it hasn’t worked so far. Can you please help?

— Single Guy Forever? West Kildonan

Dear Single Guy: It’s time to expand your role with women you’re attracted to. Get to know them on both a fun and serious level, sharing your personal life, family history and other interests.

But to really connect with someone on a deeper level, it’s time to lower your guard and actually open up about some of your own desires and even to explore some of your own fears and life challenges with them.

Also talk about the fun and adventurous things you’ve done and new things you’d like to try with a mate. Sharing specific things about yourself encourages people to be curious and want to get to know more of you. Best of luck!

Dear Miss Lonelyhearts: I just found out a woman I used to work with at a smaller drugstore is coming over to join the staff at the current (and much larger) pharmacy I now work at, and she’s divorced and free now!

When we worked together before, she was unhappily married to an idiot, but now she’s really grown up a lot, in a nice way. Who knew it would end up like this with her falling right into my lap? She is pretty amazing!

I won’t be able to pretend I don’t want her — and in every way you can imagine.

Don’t bother lecturing me about losing my new boss’s good favour. He gets around himself, I hear. I just need to know how to best handle it — and him, in case he’s competition — when she starts working here.

— Ready for Action, St. Boniface

Dear Ready: Confidence is attractive, even more if both people are interested in playing the romance game.

So talk to a friendly co-worker from your previous workplace and get the scoop on this woman’s current relationship status before she starts at your workplace. She may already be seriously involved in a relationship, so you need to know.

You seem confident a second flirtation campaign has a good chance of succeeding, now that you’re both single.

Even though you’re obviously excited, don’t make the mistake of coming on too strong. It can be a real turn-off. Plus, you can bet your new bosses don’t want to see a big romance in bloom.

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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