Why not throw Hail Mary for your old love?

Advertisement

Advertise with us

DEAR MISS LONELYHEARTS: I went to a school reunion this summer and it sucked because I was too chicken to ask my old love out. I’ve been dying to contact her ever since. She looked so amazing and sounded even better at the different get-togethers.

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 05/09/2025 (348 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I went to a school reunion this summer and it sucked because I was too chicken to ask my old love out. I’ve been dying to contact her ever since. She looked so amazing and sounded even better at the different get-togethers.

In the end we talked for two hours straight and ignored everybody else. Then we went out in the field behind the school — the place where we had once kissed and said “I love you” after my team won the football final. I was a big hero in those days.

I know where she works and where she lives now, but she told me in a regretful tone at the reunion that she had a boyfriend, though she added that he was not a keeper.

I didn’t respond because I was too choked to say, “Phone me when you punt that loser.” My heart was beating out of my chest.

She scribbled her contact info on my reunion program. Was she giving me a hint before she left? Should I call her, now that more than a month has passed? She’s likely still with the boyfriend. What if I get shot down?

— Itching to Call First Love, Charleswood

Dear Itching: Don’t let fear of a possible “No, thanks” get in the way of a possible “Yes, I’d love to see you.”

Your chances seem pretty good here — she did give you an obvious hint. So, call her before she lets Mr. Just OK go and finds someone else who is once again, not you, because you didn’t seem that interested — again. Your heart may have been beating hard, but you didn’t take her hint in the field at the reunion.

So phone her today at any hour you have the courage. If she wants to see you, she’ll be excited to hear your voice.

Dear Miss Lonelyhearts: I’m a bisexual woman and my new boyfriend is letting that fact get in his way. I’m serious about getting serious with him, but he’s worried I’ll get bored and maybe want to see another woman at the same time, like it’s a treat.

I understand his worry to a degree, but I would love him the most.

Still, I wouldn’t want to be deprived of having another woman for my whole life. So what now?

— Bi-Woman’s Problem, Winnipeg

Dear Problem: For now, you might consider enjoying your time together, knowing it’s likely not going to end up in marriage. Then, let go of each other as gracefully as possible when the time comes. Just don’t chop off the relationship prematurely.

Give it a long enough run that you’re getting weary of the limitations or, despite your current expectations, he surprises you and becomes more comfortable with what you may need.

In time, you will probably both want to be free, to find someone totally suitable. Sadly, you can’t guarantee you’ll both want your freedom at the same time.

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

Housing the homeless safely, for all

Editorial 4 minute read Preview

Housing the homeless safely, for all

Editorial 4 minute read Friday, May. 8, 2026

It’s clear that finding homes for the homeless is not as simple as saying, “Here’s a homeless person, here’s a vacant apartment, match the two of them up and voila! One less person who is homeless.”

Why?

Because the reasons a person finds themselves on the streets can be the result of long-lasting trauma or mental health issues, and even the effects of homelessness on individuals can build its own issues.

That means the process of getting someone off the streets can be extremely involved — simply finding a home is not a magic solution all on its own.

Read
Friday, May. 8, 2026

Norway takes Olympic gold in 3-way sprint in biathlon relay

Martha Bellisle, The Associated Press 3 minute read Preview

Norway takes Olympic gold in 3-way sprint in biathlon relay

Martha Bellisle, The Associated Press 3 minute read Saturday, Feb. 5, 2022

Online shopping: Alibaba vs. JD.com

Read
Saturday, Feb. 5, 2022

Al Simmons releasing his Barber of Seville adaptation

Ben Waldman  7 minute read Preview

Al Simmons releasing his Barber of Seville adaptation

Ben Waldman  7 minute read Tuesday, Mar. 16, 2021

Al Simmons needs an audience. To the beloved Manitoban children’s entertainer, butts in seats are almost as crucial as well-placed puns. Many performers make themselves the centre of attention or the ultimate decision-maker, but what’s made Simmons an icon for over 50 years is that he does precisely the opposite: he lets the audience participate, inviting five-year-olds to sing with him, heckle him, and sometimes, stage bomb him.

“In front of an audience, they become my directors. That’s what I’ve done my whole career: I hear when they laugh, and I hear where they don’t,” says Simmons, now 72. “I instruct the audience at the beginning that I expect them to yell things at me, to laugh at me, to have fun. I encourage hecklers. It just makes everybody remember: Hey, I’m watching a live performance.”

Take an archival clip from 1980. At Assiniboine Park, the Human Jukebox stands tall and attracts a dense crowd, wondering who or what is inside. A coin is dropped into a Rube Goldbergian slot, rolling through a tube. The audience is quiet, until a hand pops through to catch it. A child screams, a bell dings, and out pops Simmons. “Now for this tune, I’m going to use a very special horn,” he says. “The noise of this horn comes out of your mouths. When I squeeze it, you all go, ‘HONK.’” They oblige.

There’s real artistry at play when Simmons performs live, which is why the last 12 months have been such a strange, inexplicable era in his life. 2020 was supposed to be the busiest year of his career, but it came screeching to a halt with the pandemic, right after a run of his one-man production of Rossini’s opera The Barber of Seville wrapped up in Manitoba schools. (He developed the show with Manitoba Opera in 2009, and has toured it for the organization since).

Read
Tuesday, Mar. 16, 2021

A Manitoba pharmacist has been hit with $100,000 in fines and costs after a disciplinary panel found he dispensed a “staggering” amount of drugs that could not be accounted for.

Glen Pauch, who worked at a Portage la Prairie pharmacy, was fined the maximum $25,000 by the College of Pharmacists of Manitoba and ordered to pay another $75,000 toward the cost of the investigation and disciplinary proceedings.

A 28-page disciplinary decision, dated June 9, found more than 39,000 doses went unaccounted for while Pauch was consuming drugs and improperly dispensing controlled substances — including opioids oxycodone and hydromorphone, and Concerta, a stimulant prescribed for ADHD — to 11 patients.

The college found Pauch failed to properly document the drugs he dispensed and did not maintain required records for controlled substances returned to the pharmacy or received from suppliers.

Close to 5,000 net new health-care workers added since 2023 election, province says

Chris Kitching 6 minute read Preview

Close to 5,000 net new health-care workers added since 2023 election, province says

Chris Kitching 6 minute read Updated: Yesterday at 6:43 PM CDT

More doctors and nurses are working in Manitoba than ever before but health-care challenges remain, Premier Wab Kinew says.

The province has added 4,725 net new health-care workers to the provincial system since the NDP won the October 2023 election, Kinew told reporters Tuesday.

The government’s total includes 370 doctors, 1,464 nurses, 2,152 health-care aides and 607 allied health professionals, a group that includes physiotherapists, dietitians, paramedics, medical lab technologists and others.

Kinew said more doctors and nurses are working in Manitoba than ever before.

Read
Updated: Yesterday at 6:43 PM CDT

Improving building standards

Jean Clipsham 4 minute read Yesterday at 2:00 AM CDT

As I was working in my garden today, I was thinking that, while I still enjoy it, I am starting to wonder how much longer I will be able to care for a house and a yard. Like many my age, I have been thinking about the condominium option here in Winnipeg.

I am a mother and a grandmother and I am also very concerned about climate change and the need to recognize that our emissions from coal, oil, and gas are warming the Earth. As a climate activist, I do not want to pollute. Yet as a condo purchaser, I would have no control over how the building is insulated, heated and cooled or how much energy it would take to do so.

When I moved to Winnipeg four years ago, I intended to buy a house and install a heat pump, which heats and cools a home using electricity only.

Before that purchase, I phoned Manitoba Hydro and was advised to buy a home built after 1985, when national standards were upgraded to require better insulation. That was no trouble for me, given I had already moved from a 1960s house into a new house in 1989 and even though the new home was larger, our gas bill was cut in half because of the added insulation.