Stay away from buddy’s hot mom

Advertisement

Advertise with us

DEAR MISS LONELYHEARTS: My new friend’s gorgeous mom got pregnant and had him at 16, marrying his father at 18. The wedding party was the best part of the marriage. The rest didn’t go so well and the marriage was soon over. They were both way too young. Basically, my friend’s grandparents raised him and he lives there, in their fancy basement suite to this day.

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 21/10/2019 (2530 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: My new friend’s gorgeous mom got pregnant and had him at 16, marrying his father at 18. The wedding party was the best part of the marriage. The rest didn’t go so well and the marriage was soon over. They were both way too young. Basically, my friend’s grandparents raised him and he lives there, in their fancy basement suite to this day.

It’s confession time. My friend was dropping off a heavy chair for his mom and I was with him helping out, and I met her — his beautiful mom. It was mind-blowing. He is 20 and she is 36 or 37 now — but looks like she’s in her late 20s, more like how a sister would look.

I am well-built and tall, look older for my age and have dated women in their early late 20s. I was knocked out by how beautiful she was. She looked me up and down and gave me a devastating smile and off she went to work. Now, I can’t get her out of my mind. What should I do?

— Dreaming About Her Now, River Heights

Dear Dreaming: You should keep your buddy, but stay far away from his mom. Compare this feeling you have for her to crushing on a music or movie star. You feel a big attraction, but the object of your affection is inappropriate and out of reach.

For many reasons, you should stay away from this woman, including the fact her son might notice your obvious interest and that would be bad for him and possibly end your friendship.

Yes, this woman is beautiful and sexy, but she is his mom. How would you feel if a buddy of yours had the obvious hots for your mother and started flirting with her?

Find excuses not to go to her house again for anything and let the memory of her beauty fade. That shouldn’t be too difficult since your friend doesn’t live there and you didn’t even talk with his mom.

 

 

Dear Miss Lonelyhearts: At a big neighbourhood Thanksgiving dinner party, I ran into an old boyfriend of mine who had to know he was being invited to the same party as I would be. He grabbed a seat next to me at one of the big, extended dining-room tables and I was not happy.

I know him from our past relationship to be an under-table groper. Sure enough, after a few glasses of wine, I felt his hand coming over, resting on my leg in a “friendly” manner. I remember that move.

Instead of making a fuss — like squealing and slapping his hand — I asked for the turnips and put some on my plate and then took a big spoonful in my hand and smeared orange turnip on his thigh! He looked down and freaked and took off for the bathroom.

When he came back, he saw that my sister — at my request — was sitting in his seat. He just glared at me, walking out the door with a wet pant leg into the cold. Ha!

The next day, he phoned and left me a nasty, very vulgar message. Do I have anything to worry about?

— Nervous Ex, St. Boniface

 

Dear Nervous: Not to worry. He probably feels he got you back with the vulgar message and you can just block his number now. His hand on your thigh was also a vulgar message, so he’s more than even.

 

 

Dear Miss Lonelyhearts: I had a terrible time at Thanksgiving dinner because I don’t get along with my parents. They are the rudest people in the world and at 9 p.m., my father announced it was time for everyone to “hit the road” because he had a big day the following day.

I looked at my boyfriend and he raised his eyebrows and I just shrugged and he went and got our coats. He asked me if my family was always cold and rude and I had to say, honestly, they are. He said, “At Christmas, you are coming to my house, as I don’t want ever to go back to your parents’ house again.” Never is a long, long time.

Miss L., they are family, and I do love them, flawed as they are. I can’t change their behaviour, though I have tried. Is it dangerous to get involved with a guy seriously, who will only see his family and never mine? He wouldn’t want our children — should we have any — to spend much time with them, or maybe none.

He is quite controlling, but maybe that would change as our love grows. What do you think?

— Considering Break-Up, Tuxedo

 

Dear Considering: If you already know a romantic partner is controlling, you are wise not to marry them. You don’t want to find out this guy decides everything for you and the family — and you have to remain quiet to keep the uneasy peace. You’ve had your warning now.

You really need a different guy with a sense of humour who sees your folks for what they are and knows how to do a few things to loosen them up.

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

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

Door-knocking trustee candidate calls for changes to expansive boundaries

Maggie Macintosh 4 minute read Preview

Door-knocking trustee candidate calls for changes to expansive boundaries

Maggie Macintosh 4 minute read 8:14 PM CDT

John Baert wants all the school trustee candidates who follow in his footsteps to have far less ground to cover.

The Island Lakes father said he was, in retrospect, “naive” when he launched his campaign in the Louis Riel School Division.

“When I started knocking on doors, I had a goal to hit every single door in the ward,” said the nominee for Ward 4, which encompasses Royalwood, Southdale, Sage Creek and Island Lakes.

More than one million steps later — Baert’s Garmin watch has been tracking his canvassing efforts on evenings and weekends since mid-July — he is about 60 per cent of the way to his goal.

Read
8:14 PM CDT

Puzzles Palace

1 minute read Monday, Jul. 27, 2026

To solve our puzzles, please subscribe with this special offer: |

Kinew, NDP rise to new heights in Free Press-Abacus Data poll; support for Khan, Tories falls further

Chris Kitching 6 minute read Preview

Kinew, NDP rise to new heights in Free Press-Abacus Data poll; support for Khan, Tories falls further

Chris Kitching 6 minute read Monday, Sep. 21, 2026

Buoyed by a bump outside Winnipeg, support for Premier Wab Kinew’s NDP climbed to its highest level yet, while the Tories lost some ground.

Read
Monday, Sep. 21, 2026

Even dozen running for mayor as nomination deadline passes

Malak Abas 2 minute read Preview

Even dozen running for mayor as nomination deadline passes

Malak Abas 2 minute read Yesterday at 6:25 PM CDT

It’s official — a dozen people are running to become Winnipeg’s next mayor.

The deadline to both register to run as a candidate in October’s municipal election and file nomination papers was 4:30 p.m. Tuesday.

The final list of mayoral candidates includes: incumbent Scott Gillingham, Kevin Klein, Brad Gross, Mazher Alam, Mike Vogiatzakis, Christopher Clacio, Umar Hayat, Don Woodstock, Joshua Pagdato, Johnny Calderon, Noah Redden, and Tracey Drexler.

A total of 17 had registered to run but several either withdrew or did not meet the requirements to continue. Those included: Zachary Uminski, Ed Ackerman, Gagandeep Bawa, Abdel-Kareem Chehadi and Joaquin Sandul.

Read
Yesterday at 6:25 PM CDT

Driver, 62, killed in highway crash

1 minute read 10:25 AM CDT

One person was killed and a second was injured in a crash involving an SUV and semi-truck just outside Sanford on Tuesday morning.

RCMP said the semi-truck was eastbound on Highway 3 when it collided with the SUV, which was being driven south on Provincial Road 334 by a 62-year-old Sanford man, who died at the scene.

The collision happened shortly after 5 a.m.

Police said the semi-truck’s driver, a 58-year-old Morden man, was treated for non-life-threatening injuries.

Relief, reproach from law school staff after disgraced ex-dean’s arrest in France

Maggie Macintosh 5 minute read Preview

Relief, reproach from law school staff after disgraced ex-dean’s arrest in France

Maggie Macintosh 5 minute read 5:43 PM CDT

The overseas arrest of a disgraced former law dean who defrauded the University of Manitoba out of more than $600,000 is being met both with relief and renewed frustration in the local legal community.

Read
5:43 PM CDT