You’re free, but don’t get ahead of yourself, Romeo

Advertisement

Advertise with us

DEAR MISS LONELYHEARTS: I love people’s second marriages, where two people who first made mediocre choices finally marry their way-back loves. I really need to do the same thing. There’s nothing wrong with my wife, except for the fact she packed up and left me. Apparently I am a colossal bore.

Read this article for free:


or

Already have an account? Log in here »

To continue reading, please subscribe:

Subscribe and receive a limited-edition Free Press branded hat or tote.

Digital Subscription

One year of digital access for only $205*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles

*First annual payment billed as $205.00 + GST for one year. This annual subscription will automatically renew at $233.00 + GST every 52 weeks (10% off the regular annual price of $259.35). Offer available to new and qualified returning subscribers only. Cancel any time.

To continue reading, please subscribe:

Add Free Press access to your Brandon Sun subscription for only an additional

$1 for the first 4 weeks*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles
Start now

*Your next Brandon Sun subscription payment will increase by $1.00 and you will be charged $17.95 plus GST for four weeks. After four weeks, your payment will increase to $24.95 plus GST every four weeks.

Opinion

Hey there, time traveller!
This article was published 08/09/2025 (391 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I love people’s second marriages, where two people who first made mediocre choices finally marry their way-back loves. I really need to do the same thing. There’s nothing wrong with my wife, except for the fact she packed up and left me. Apparently I am a colossal bore.

What a wake-up call. She had never really been the one I truly desired either. Truth be told, I actually preferred her sister.

Then I got another happy shock when I learned an exciting married woman (there had been some serious mutual flirting between us in the past) just pulled herself free from her soul-sucking husband.

Now I want to show up at her place some night in a hot convertible, honking my horn and yelling, “Hey, babe — come on out and jump in. Let me take you on a wild ride.”

What do you think — am I too old to do something like this? Sometimes I feel drunk on possibilities, but I need some good advice as I set out on my new adventure.

— Time to Follow Heart, rural Manitoba

Dear Time to Follow: You are just the right age to yell whatever makes you feel good again. To show this woman the “wild man” in you, first take her out on a fun date — some surprise she would really enjoy that you’ve planned for her.

If things go well, on the next date, get caught up on both your lives, sharing stories parked under the moon somewhere. You’ll soon find out if she thinks you would still be a fun match.

It could be great start to something, or she could be a bomb, and the same for you from her perspective. It depends on how you’re feeling coming out of your respective marriages and if the two of you are compatible.

So don’t get ahead of yourself here — what you need is a mix of maturity and youthful spirit, and communicate your real feelings and opinions on life. (And make sure to avoid criticism of your exes.)

Just because the two of you are out of unhappy marriages doesn’t mean a magical relationship is just going fire up — it takes some real work and honest communication.

Dear Miss Lonelyhearts: I could not be more shocked. My recent ex (a female) is seeing a number of people now, and only one of them is a monogamous guy.

The two others are with her in what I can only describe as a novel sort of three-way to “try out new things,” as she explained to me.

Why couldn’t she have done this with me? I’m an open-minded, good-looking guy. I was always up to experiment with her and someone else, but she curled her lip at that.

I was so willing — maybe a bit too much. What does it take?

— Puzzled, West Kildonan

Dear Puzzled: It takes a medium-close couple to experiment together — a duo who think the same way and have similar tastes in new people, and in the sexual adventures they would like to explore. It could be that you were a bit too eager, or maybe she just didn’t think your personality was good fit for this sort of thing.

It’s also something that may not work for a close, committed couple looking forward to one day being in a tight one-on-one relationship with a view to starting a family together.

In other words, you need playmates who want to remain playmates. Jealousy is the enemy in these multi-element couplings, so you don’t want to get too intimately entwined with playmates who could provoke those hurtful feelings.

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.

Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.

Report Error Submit a Tip

More Stories

Volunteer pop-up library axed from Manitoba Youth Centre

Matthew Frank 3 minute read Preview

Volunteer pop-up library axed from Manitoba Youth Centre

Matthew Frank 3 minute read Updated: 11:25 AM CDT

Manitoba Corrections has cancelled a pop-up library program at the Manitoba Youth Centre, leaving inmates without librarian services and fewer options to borrow certain books.

The Prison Libraries Committee, part of the non-profit Manitoba Library Association, operated and funded the volunteer program since 2024 before it was shut down by the province last month. The group previously partnered with the province to offer the service because the facility has no dedicated library of its own.

“It is concerning that community members who are incarcerated, especially youth, are losing out on meaningful programming, access to information and rehabilitation efforts, which are offered at no cost to (Manitoba) Corrections. We urge Manitoba Justice to promote more library services and programming, not less,” said a Sept. 24 letter from the non-profit addressed to the justice minister.

Ashley Huot, chair of the Prison Libraries Committee, said she was puzzled when she received an email last month from Manitoba Corrections stating that the pop-up library was no longer needed.

Read
Updated: 11:25 AM CDT

Broadening prediction-market gambling a bad idea

Editorial 4 minute read Preview

Broadening prediction-market gambling a bad idea

Editorial 4 minute read 2:01 AM CDT

Let’s make a prediction: sooner or later, when Canadian governments find a way to take their own cut of the action, prediction-contract gambling on everything from sports to entertainment to political decisions is going to come to Canada.

And that’s a horrible, dangerous, pernicious idea.

Unless you have particular access to information — either inside information or strategic information based on skills or education — you’re not likely to make money at it. In fact, structurally, you’re likely to lose. In prediction markets, you basically pay an amount, plus fees from the company involved, to bet on whether something will or will not happen within a certain time frame. The amount you pay for your contract depends on how other people are also betting.

As Wealthsimple describes it, “You buy whichever side you think is right. Prices move with demand, so if the market leans towards one outcome, the more that side costs. If a lot of people are backing the TSX to finish above 38,000, yes gets more expensive and no gets cheaper.”

Read
2:01 AM CDT

Retired guidance counsellor defends explicit 2025 sex-ed presentation to high school football team in disciplinary hearing

Maggie Macintosh 6 minute read Preview

Retired guidance counsellor defends explicit 2025 sex-ed presentation to high school football team in disciplinary hearing

Maggie Macintosh 6 minute read Updated: Yesterday at 12:26 PM CDT

Gus Watanabe, a former employee of Oak Park High School in Winnipeg, was the subject of a public disciplinary hearing on Thursday.

Read
Updated: Yesterday at 12:26 PM CDT

Health minister warns $1.2 billion in annual federal funding set to expire in March

Scott Billeck 3 minute read Preview

Health minister warns $1.2 billion in annual federal funding set to expire in March

Scott Billeck 3 minute read Thursday, Oct. 1, 2026

Manitoba’s health minister is warning of possible cuts to health care with $1.2 billion in annual funding from Ottawa set to expire next year.

“We’re very concerned that what would be the largest cut to health care in a generation is right in front of us,” Health Minister Uzoma Asagwara said Thursday at the Manitoba legislature. “It means that services that Manitobans depend on will be in jeopardy and be at risk.

“Any reductions, any cuts from Canada, will have direct impacts on the health outcomes of Manitobans.”

Asagwara, who serves as the provincial and territorial health minister lead, chaired a virtual meeting Tuesday with provincial and territorial health ministers to discuss federal funding for health care, mental health care and substance use services, which is scheduled to expire March 31, 2027.

Read
Thursday, Oct. 1, 2026

J’accuse!: Kinew uses French to fry interim Tory leader over alleged caucus subterfuge

Chris Kitching and Maggie Macintosh 3 minute read Preview

J’accuse!: Kinew uses French to fry interim Tory leader over alleged caucus subterfuge

Chris Kitching and Maggie Macintosh 3 minute read Thursday, Oct. 1, 2026

NDP Premier Wab Kinew took a dig at the Progressive Conservatives’ leadership change while facing off with Obby Khan’s short-term replacement for the first time in question period Thursday.

Read
Thursday, Oct. 1, 2026

Sisters relieved hospital takes accountability after mother’s death

Scott Billeck 5 minute read Preview

Sisters relieved hospital takes accountability after mother’s death

Scott Billeck 5 minute read Thursday, Oct. 1, 2026

Eight months after losing their mother, two Winnipeg sisters say an internal hospital review has finally given them something they had been seeking since her death: accountability.

Chelsea Mann and Samantha Burns said St. Boniface Hospital officials acknowledged mistakes were made in the care of their mother, Judy Burns, during a recent meeting to discuss the findings of a critical incident review into her death.

The acknowledgement marked a significant departure from an earlier meeting with hospital officials, when they felt their concerns were largely dismissed.

Burns, 68, died on Jan. 21, three days after being admitted, after experiencing rectal bleeding.

Read
Thursday, Oct. 1, 2026