Kid-sitting for sis could be win-win prospect

Advertisement

Advertise with us

DEAR MISS LONELYHEARTS: I’m a relatively young middle-aged guy in my 30s from a big business family, and I’m feeling more than ready to find a wife and start a family.

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.

DEAR MISS LONELYHEARTS: I’m a relatively young middle-aged guy in my 30s from a big business family, and I’m feeling more than ready to find a wife and start a family.

I have a lot of money saved, and I own my own house, but I have no love partner this year as I was closing some deals with my dad. I often worked 18-hour days and was out of town for months on end.

That’s completed now and it was very successful, so now it’s back to normal in Winnipeg.

However, I can now afford to take regular time off and get back to eight-hour days and pretty much set my own hours.

Then my sister — an executive secretary — got pregnant unintentionally earlier this year. She plans to have the child on her own and I’m jealous.

She knows my situation and has offered to hire me for morning infant care so she can work part-time.

I’m used to being home in the mornings and working one to nine p.m., so she thinks it could work. Or, would it just rub it in for me that the child isn’t mine and I’m just the uncle? I did a lot of babysitting as a teenager and was really good at it. I need your advice.

— Longing For Kids and Family, Winnipeg

Dear Longing: Trying out the babysitting deal with your sister’s kid would be a serious experiment that might help you come to more reality-based conclusions about what you really want and need in the long-term, such as combining work and raising children.

This experience will also be intriguing to the type of family-oriented woman you might like to date. You might be very popular with the other women pushing their little ones around in the park, and they might have some interesting single friends.

It sounds like a worthwhile experience and a great way to bond with your future niece or nephew, so why not try it?

Dear Miss Lonelyhearts: I’m dating a woman who personifies bodily perfection. My dad met her recently and is not impressed. He says it looks like she’s trying to get her hooks into me by “parading her fit body and fake tan.”

He says it doesn’t sound like a deep and lasting love prospect to him.

He knows I want to get hitched, and he’s a lucky guy who has been married forever to a great woman — my mom.

Is he right, or just a jealous old codger who’s trying to spoil my fun?

— Tired of Being Lonely, River Heights

Dear Lonely Guy: Dad knows his son well and may be sensing some warning signs. This woman trying to win you with her body perfection is not impressing him.

Why are you panicking, anyway? Rushing things can get you into a very quick and unhappy relationship, making you feel worse than lonely.

So slow down and see how things actually progress in your relationship. Don’t totally discount your father’s concerns and don’t be too starry-eyed and hasty either.

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

Rise of social media reflects rise of self-promotion — to the detriment of genuine storytelling

Reviewed by Matt Henderson 4 minute read Preview

Rise of social media reflects rise of self-promotion — to the detriment of genuine storytelling

Reviewed by Matt Henderson 4 minute read 3:00 AM CDT

A conversation is overheard between two people; one congratulates the other on their success, evident through countless posts on LinkedIn, but the other confesses the prolific aggrandizement is due to slumping success.

A young man on an airplane spends three hours poring over selfies taken on a vacation, zooming in on his biceps and using AI to retouch photos before posting on Instagram.

Anonymous and cowardly trolls on Reddit attempt to end another person’s career.

All this “storytelling” was observed in one day by this reviewer.

Read
3:00 AM CDT

Nola chef earns national award

Eva Wasney 2 minute read Preview

Nola chef earns national award

Eva Wasney 2 minute read Yesterday at 2:01 AM CDT

Celebrated Winnipeg chef Emily Butcher has another feather to add to her toque. The executive chef and owner of Nola and Bar Accanto in St. Boniface has received the Culinary Award of Excellence from Restaurants Canada, a national foodservice advocacy organization.

Read
Yesterday at 2:01 AM CDT

Trailblazing Western Scrap Metals heavy-equipment operator relishes role at massive crane’s control

David Sanderson 7 minute read Preview

Trailblazing Western Scrap Metals heavy-equipment operator relishes role at massive crane’s control

David Sanderson 7 minute read Yesterday at 10:15 AM CDT

Less than five per cent of heavy-equipment operators in the country are women but that number is trending upward, according to a study conducted by trade magazine Crane & Hoist Canada.

It was reported that in Ontario roughly eight per cent of jobs in the transport and heavy-equipment field are currently held by women. Furthermore, in 2024 almost 20 per cent of graduates at an Edmonton-based heavy-equipment operator training school were female, the article stated.

That brings us to Harmony Guspodarchuk, the first female crane operator in the 70-year history of Western Scrap Metals, a family-owned business at 18 Sutherland Ave.

Three years ago, Guspodarchuk literally stepped into the driver’s seat of a 27,500-kilogram, Liebherr C 924 Heavy Lift Litronic crane. The 29-year-old hasn’t looked back much since.

Read
Yesterday at 10:15 AM CDT

Big Loser’s latest a winning mix of country, folk

Ben Waldman 4 minute read Preview

Big Loser’s latest a winning mix of country, folk

Ben Waldman 4 minute read 6:00 AM CDT

The yellow trucker hat for sale on Facebook Marketplace said “Selkirk Lumber,” so Adam Wayne Brown knew he had to hammer home a deal.

Like the other millennial members of Winnipeg folk-country band Big Loser, the bassist has an affinity for the nostalgic, taking every opportunity — through music, through lyrics and through wardrobe — to recall the unique circumstances of growing up in a changing Interlake.

“I remember the matte yellow trucks driving around — the lumber trucks — and so I’ve had this strange memory of something disappearing from my youth and then persisting,” says Brown, who, like the band’s frontman Alex Paradoski, moved to Winnipeg more than a decade ago.

“I have a photo of the Lockport Bridge in my dining room,” chimes in Paradoski, whose first job as a teenager was bunning wieners and chopping fries at Skinner’s, a drive-in mainstay since 1929 along Highway 44.

Read
6:00 AM CDT

WRHA directs three care homes to accommodate surge of hospital patients

Malak Abas 5 minute read Preview

WRHA directs three care homes to accommodate surge of hospital patients

Malak Abas 5 minute read Updated: Yesterday at 5:01 PM CDT

The Winnipeg Regional Health Authority has directed three long-term care centres to make space for hospital patients, citing “exceptionally high demand for care across the health-care system.”

Read
Updated: Yesterday at 5:01 PM CDT

Wyatt vows to ‘absolutely’ continue serving as city councillor despite latest sex-crime charges

Joyanne Pursaga 5 minute read Preview

Wyatt vows to ‘absolutely’ continue serving as city councillor despite latest sex-crime charges

Joyanne Pursaga 5 minute read Thursday, Aug. 13, 2026

Transcona Coun. Russ Wyatt vowed Thursday to continue doing his job after more criminal charges were laid against him this week, while the mayor called for “better tools” to address elected officials who face serious allegations.

Wyatt, 56, was charged Monday with sexual assault and administering a noxious substance in an October 2023 incident. He was previously charged with sexual assault and administering a noxious substance in March, based on allegations tied to a 2025 gathering.

On Thursday, Wyatt arrived at city hall and quickly walked to his office at 10:20 a.m., nearly an hour after the East Kildonan-Transcona community committee meeting he planned to attend was scheduled to begin.

He answered few questions from reporters.

Read
Thursday, Aug. 13, 2026