Former convict trapped with unwanted roommate

Miss Lonelyhearts By: Miss Lonelyhearts Posted:

Advertisement

Advertise with us

Dear Miss Lonelyhearts: I went to jail for quite a few years. All of a sudden, this guy I had known well when I was incarcerated pulled up in a taxi and knocked on my door. He was a funny guy when I knew him, so I let him in. We had a few beers and caught up. He didn't make a move to leave. It turns out he wanted a place to stay for a few days until he got on his feet. He had just gotten out of jail again in another province. It's been a month and he's still here, staying in the small bedroom. How do I kick him out? He doesn't have a job.

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 27/04/2016 (3808 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I went to jail for quite a few years. All of a sudden, this guy I had known well when I was incarcerated pulled up in a taxi and knocked on my door. He was a funny guy when I knew him, so I let him in. We had a few beers and caught up. He didn’t make a move to leave. It turns out he wanted a place to stay for a few days until he got on his feet. He had just gotten out of jail again in another province. It’s been a month and he’s still here, staying in the small bedroom. How do I kick him out? He doesn’t have a job.

His mother, who lives in town, gives him money and wants him to stay with her, as she’s getting old and needs some work done around her place. She would also like his company and the security of having him there. Today he gave me money for room and board that I know he got from her. I don’t want it, and I don’t want him. Help! I’m a single man and need this place back for privacy, as I have a few girlfriends I would like to get back to entertaining.

— Unwanted Roomie Has To Go, West End

 

Dear Unwanted Roomie Has To Go: Tell him you have girlfriends and you need your place back so you can bring them over. Tell him the ladies are getting restless and you want some privacy. Remind him he just asked for a few days of couch-surfing, but now you need him to make a new plan, fast.

He’ll have to live with his mom for a while. If it doesn’t look like he’s in any hurry to leave, give him a deadline. Tell him you have a couple of hot dates, and set them up so it’s real and your voice has the ring of truth. He’ll feel better if he’s leaving for those reasons, not because you don’t want him. Let him save face, but still be firm. After all, mama’s door is wide open.


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

 

Miss Lonelyhearts

Miss Lonelyhearts
Advice Columnist

   Read full biography

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.

Miss Lonelyhearts

Miss Lonelyhearts
Advice Columnist

   Read full biography

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.

Related Articles

Quit your job, follow your dreams You can move around the sexual continuum Fight about affectionate cat was purrfectly silly Work out a verbal agreement, or get another fridge Expect fun times to end with Miss Saturday Night She has her cake, and eats out, too Flirting with neighbour will only to lead to world of hurt Give widow some time before making move

Advertisement Advertise With Us

Report Error Submit a Tip

Advertisement

Learn more about Winnipeg Free Press Advertising solutions

More Stories

JOHN WOODS / FREE PRESS Progressive Conservative Leader Obby Khan, the first Muslim to win a seat in the legislature, announced Monday that he is stepping down.

Khan cites infighting, quits as Tory leader

Carol Sanders 5 minute read Preview

Khan cites infighting, quits as Tory leader

Carol Sanders 5 minute read Updated: Yesterday at 9:56 AM CDT

Manitoba’s Leader of the Opposition is stepping down.

Progressive Conservative Leader Obby Khan announced late Monday afternoon he is quitting caucus and will sit in the legislature as an independent MLA, effective today.

He cited internal party fighting for his decision.

The former Winnipeg Blue Bombers offensive lineman survived a caucus confidence vote Friday. He said there were 13 votes for him to remain and six against, with one person absent.

Read
Updated: Yesterday at 9:56 AM CDT
MIKAELA MACKENZIE / FREE PRESS Emily (13, left) and Julie (eight) Sobkowicz with their family landline phone on Sept. 25. The family has used the landline to encourage the kids’ communication skills and stave off the encroachment of digital devices.

In a smart-device world, some families keep phone jacked into the wall

Sheldon Birnie 8 minute read Preview

In a smart-device world, some families keep phone jacked into the wall

Sheldon Birnie 8 minute read Yesterday at 4:20 PM CDT

When the phone rings in Kristin Shiach and Jordan Sobkowicz’s Riverview home, their three daughters race to see who can be the first to answer.

“It depends who is closest,” says 13-year-old Emily. “If I’m sitting in my room, I can get to it quickest.”

“That’s because it’s always in your room,” Anna, 10, replies. “You never put it back!”

“Usually, when the phone rings,” explains Sobkowicz, “someone yells really loudly —”

Read
Yesterday at 4:20 PM CDT

Teacher barred for ‘repeated boundary-crossing conduct’

Maggie Macintosh 3 minute read Monday, Sep. 28, 2026

A disciplinary panel has ordered the cancellation of a Chinese-Canadian teacher’s certificate because of her “repeated boundary-crossing with a student” during her tenure at an international school with local ties.

Janice Wen Ying Ma is permanently barred from teaching on Manitoba soil or at a Manitoba-accredited institution as of Sept. 14.

The new ruling concludes that Ma engaged in inappropriate physical interaction and “emotionally intimate online messages” with a girl who attended Clifford International School in Guangzhou, China in 2024-25.

“This conduct represents a fundamental departure from the standards expected of a teacher,” the panel, chaired by public representative Gordon Schumacher, wrote in its 22-page decision.

DARREN CALABRESE / THE CANADIAN PRESS FILES ‘We warn the government against abusing its majority status and dishonouring the Crown through procedural tools, time allocation or closure to frustrate Parliament’s ability to hear from rights holders and consider amendments,’ National Chief Cindy Woodhouse Nepinak says.

Canada resorting to its tried and true playbook

Niigaan Sinclair 5 minute read Preview

Canada resorting to its tried and true playbook

Niigaan Sinclair 5 minute read Monday, Sep. 28, 2026

In 1846, Britain faced an emergency influenced by the Irish famine, so leaders repealed the country’s “Corn Laws” and restrictions on imported food and grain, transitioning to a system of free trade.

This created a crisis in the then Province of Canada, which had relied on British “preferential” status to prop up its agricultural and resource industries.

As a result, Canada looked south for new markets and eventually negotiated a free trade agreement with the United States.

This required land to be acquired and converted for industrial use quickly, so Canada quickly dispatched Commissioner William Robinson to negotiate with Indigenous communities along Lake Huron and Lake Superior for land.

Read
Monday, Sep. 28, 2026

News briefs for Wednesday, September 30, 2026

3 minute read Updated: 10:42 AM CDT

A collection of breaking news briefs filed on Wednesday, September 30, 2026

Collisions send people to hospital; one fatality

10:42 AM

Five people are in hospital following a two-vehicle collision on Monday at the corner of Pembina Highway and Plaza Drive in which three pedestrians were struck.

NICK WASS / THE ASSOCIATED PRESS FILES Former Washington Capitals goalie Clay Stevenson is joining the Jets and will immediately step into the role as backup goalie.

Jets pick up netminder as relatively new 23-man roster announced

Mike McIntyre 7 minute read Preview

Jets pick up netminder as relatively new 23-man roster announced

Mike McIntyre 7 minute read Monday, Sep. 28, 2026

Let’s get the caveats out of the way: Nothing is set in stone, nor written in permanent ink, and what you see right now could change in the blink of an eye.

With that being said, allow us to introduce you to the 2026-27 Winnipeg Jets — where change is very much in the air.

The 23-man roster submitted to the NHL offices by Monday’s 4 p.m. deadline includes seven players who were not on the team at this time last year. In fact, there could be as many as 10 new faces in the opening-night lineup on Friday against Boston when you factor in three regulars didn’t start the 2025-26 campaign due to injury.

That’s a lot of turnover, which isn’t surprising for a team that finished 26th overall in the standings and was — to most fans and pundits — too old and too slow.

Read
Monday, Sep. 28, 2026