Son making moves on dad’s younger girlfriend

Advertisement

Advertise with us

Dear Miss Lonelyhearts: I have a girlfriend who’s younger than me by 11 years, and I introduced her to my 20-year-old son this summer at the cabin. My other son is 16 and just likes fishing. The 20-year-old is always finding excuses to be with my lady, challenging her to dive for things off the dock (she wears a bikini), asking her to play Scrabble with him, then rounds of rummy and singing while he plays guitar for them.

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 26/08/2017 (3323 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I have a girlfriend who’s younger than me by 11 years, and I introduced her to my 20-year-old son this summer at the cabin. My other son is 16 and just likes fishing. The 20-year-old is always finding excuses to be with my lady, challenging her to dive for things off the dock (she wears a bikini), asking her to play Scrabble with him, then rounds of rummy and singing while he plays guitar for them.

It’s enough already. I know he has a crush on her, and I have turned out to be jealous of my own son. I am in my early 40s and he is a body builder and football player, with a nice tan. I feel like Father Time when I’m around them. What do you think I should do?— His Old Man, Southdale

Dear His Old Man: This has the makings of a big disaster. How about breaking it off with the young woman? She’s co-operating in this growing problem with your son and is clearly not respecting you.

Boundaries are being crossed already (they are openly flirting), which is why you’re feeling so lousy watching it.

Save your relationship with your son and don’t bring any more hot ladies home who may be 30, but look delicious and young enough for him — especially not in bikini weather. 

 

Dear Miss Lonelyhearts: I was introduced to a good-looking, charming man with a bit of a reputation in town. I was feeling bored this summer after a breakup, so decided to go out for dinner with him, for a laugh. I expected him to be a leering jackass, but he was nothing of the sort. He was a gentleman — kind, respectful, intelligent and a great kisser, though a bit of a sex tease. (He wouldn’t have intercourse.)

He told me I wasn’t the usual kind of woman he went out with, but he was making an exception because I was special in some way he couldn’t put his finger on. I wanted to know what I was lacking and what was making up for it that was special. I became obsessed!

I was out golfing the other day and had a bite to eat with my friend at a restaurant, my new guy’s favourite spot. While my friend went to the bathroom, I was eavesdropping on the next table.

I overheard this woman, about my age, describe her new man to her girlfriend. She was puzzling over this thing he had said to her. It turned out to be exactly the same thing my new guy had said to me, word for word! When she got up to go, I took a secret photo of her with my phone.

He called me this evening and I couldn’t wait to go out with him. I suggested the same place where I had overheard the conversation, and he seemed a bit uneasy. When we got there, I was in a rare mood. I had something light, since I wasn’t planning to stay long. He told me I looked especially buoyant.

I said I was and wanted to play a game called guess who made this remark, and he looked at me kind of funny. Then I quoted the same line he used with that other woman and me.

As he sat there stunned, I pulled out my camera and photo of the other woman, and said, “She doesn’t know what to make of that line either.”

Then the gentlemanly veil came off. He called me “an insecure, sneaky, little bitch!” and walked out, leaving me with the bill.

I just wanted to pass that line along to any other Winnipeg women who might run into this “charming” guy. Why is that line so effective? — Just Wondering, Winnipeg

Dear Just Wondering: Rather than give you a feeling of security, this guy issues a challenge off the top. You’re not told what the challenge is, except you’re lacking in some way, and must make up for it if you are to win his heart, when so many others have not. That way he doesn’t look like he needs any woman, and his dates will work harder to impress him.

He likes to make women feel they’re lucky to even be in his company, and his body and heart are used as bait. But he had gotten lazy and started using the same old line.

You can bet he’ll be working on a new line to replace it now. There is no point in being genuine and letting a woman get close.

 

Dear Miss Lonelyhearts: My husband and I are in our mid-20s and need some new friends. We are in a fairly new development and we have ended up in a couples-with-young-kids crowd.

Our parents helped us with a mortgage and we feel kind of beholden to them, although neither of us really wanted to live here. Our parents chose the place, more or less.

We want to go back to Osborne Village, where we’ve always lived since we left home. We don’t want kids for the next five years at least — maybe never — and we miss the uptown feel of an apartment there.

We hate it here in the burbs! We just don’t know how to tell our parents, so what do you suggest?— Ungrateful Kids, Winnipeg Suburb

Dear Ungrateful Kids: There’s nothing left to do except tell your two sets of parents you’re selling the house in the suburbs and giving them back the money they gave you for the mortgage, although you are going to have to eat some expenses yourselves in terms of closing costs.

You must act like adults now. You’ll have to stand up to some hassles going through this and perhaps the accusations you fear of being ungrateful. But hold your ground. Do what makes you happy as a couple and only apologize to each other for not being stronger sooner.

Assure the parents they’ll get all their money back. Suggest the folks go on a big cruise together with the mortgage moolah.

 

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

What’s open, what’s closed, what’s up in Winnipeg on National Day for Truth and Reconciliation Sept. 30, 2026

Free Press staff 4 minute read Preview

What’s open, what’s closed, what’s up in Winnipeg on National Day for Truth and Reconciliation Sept. 30, 2026

Free Press staff 4 minute read Sunday, Sep. 27, 2026

The National Day of Truth and Reconciliation, or Orange Shirt Day, as it's known in Manitoba, happens Sept. 30 with many commemorative community events scheduled.

Read
Sunday, Sep. 27, 2026

Now-independent ex-Tory leader skips legislature’s first question period in four months

Chris Kitching 5 minute read Preview

Now-independent ex-Tory leader skips legislature’s first question period in four months

Chris Kitching 5 minute read Tuesday, Sep. 29, 2026

Crime rates, the cost of living and the state of health care were on the agenda Tuesday when the legislature’s fall sitting began a day after Obby Khan’s abrupt resignation from the Tory caucus.

Read
Tuesday, Sep. 29, 2026

Man charged after drugs, thousands of dollars seized

2 minute read Yesterday at 10:17 AM CDT

A 24-year-old man has been charged with numerous offences following a drug trafficking investigation by Winnipeg police.

In September, the Organized Crime Unit (OCU), initiated an investigation involving an individual and a residence in the 300 block of Stradbrook Avenue.

On Sept. 22, with the assistance of the Tactical Support Team (TST) and the Central District Community Support Team, officers attempted a traffic stop on a vehicle. The driver refused to stop and fled, colliding with another vehicle. A suspect was arrested a short time later after a brief foot pursuit. No injuries were reported as a result of the motor vehicle collision.

Subsequent search warrants were executed on the suspect’s vehicle and a residence on Stradbrook. Officers seized three ounces of cocaine (estimated street value $6,000); approximately $30,000 in Canadian currency; approximately $13,000 in counterfeit currency; packaging and other illicit drug paraphernalia; a scale; a vacuum sealer; fraudulent photo ID; and three cellphones.

‘We’ll stand for the children’: crowds gather for Orange Shirt Day in Winnipeg

Matthew Frank 5 minute read Preview

‘We’ll stand for the children’: crowds gather for Orange Shirt Day in Winnipeg

Matthew Frank 5 minute read Updated: Yesterday at 6:08 PM CDT

A sea of people clad in orange shirts and waving flags marched through downtown Winnipeg to honour those who survived and died in residential schools.

Read
Updated: Yesterday at 6:08 PM CDT

Obsessed stalker who shot, killed young woman at bus stop in 1993 dies behind bars at age 74

Erik Pindera 3 minute read Preview

Obsessed stalker who shot, killed young woman at bus stop in 1993 dies behind bars at age 74

Erik Pindera 3 minute read Tuesday, Sep. 29, 2026

A Winnipeg man who stalked a woman for several years before shooting her dead in the street in 1993 has died in Stony Mountain prison.

On Monday, 74-year-old Ronald Edd Bell died of apparent natural causes at the federal prison just north of Winnipeg, the Correctional Service of Canada said.

Bell had been in prison since May 30, 1994, when he was given a life sentence with no chance of parole for 18 years for killing Terry-Lyn Babb, 25, on Jan. 21, 1993.

Bell walked up behind an unsuspecting Babb, who was waiting at a bus stop at Sherbrook Street and Wolseley Avenue, and shot her in the head with a pistol in front of horrified witnesses, says the Free Press report of his sentencing hearing.

Read
Tuesday, Sep. 29, 2026

Woman took ‘meaningful’ responsibility after disposing of body: lawyer

Dean Pritchard 4 minute read Preview

Woman took ‘meaningful’ responsibility after disposing of body: lawyer

Dean Pritchard 4 minute read Yesterday at 6:00 AM CDT

A woman who was threatened with death if she didn’t help dispose the body of a Mexican man murdered in the basement of a North End home should serve no more jail time, a judge has been told.

Devlin Langlois, 25, has pleaded guilty to accessory after the fact to murder in the March 2025 killing of 28-year-old Diego Moscoza.

“By pleading guilty, Ms. Langlois has already taken meaningful accountability for her actions,” defence lawyer Joshua Rogala told King’s Bench Justice Candace Grammond at a sentencing hearing Monday.

He urged the judge to sentence Langlois to the equivalent of 14 months already served, plus two years supervised probation.

Read
Yesterday at 6:00 AM CDT