Threesome’s a crowd

Advertisement

Advertise with us

Dear Miss Lonelyhearts: I just met a cute older guy online, and he asked me out on a date. He asked if he could bring a female friend, and I joked, "Are you that scared of me?" He brought a friend all right, and they were looking for a threesome. I burst out laughing nervously and walked out. When I said in my profile that I like lots of people and have a lot of female friends, I didn't mean I wanted to play games with them in bed. What a nervy thing to bring her along! I didn't say much, and just left. Was that the right thing to do?

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 13/06/2016 (3744 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I just met a cute older guy online, and he asked me out on a date. He asked if he could bring a female friend, and I joked, “Are you that scared of me?” He brought a friend all right, and they were looking for a threesome. I burst out laughing nervously and walked out. When I said in my profile that I like lots of people and have a lot of female friends, I didn’t mean I wanted to play games with them in bed. What a nervy thing to bring her along! I didn’t say much, and just left. Was that the right thing to do?

— Three’s A Crowd, Transcona

 

Dear Three’s a Crowd: They probably had a big laugh. I doubt they were shocked or upset. It was a nervy chance to take, and they knew it. But why didn’t you catch on when this guy asked if he could bring a woman? That was a pretty big hint, and 19 out of 20 women would have said, “I’m not going to meet you now.” Did you really think he was kidding? Or were you intrigued?

 

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

Retired sportscaster Scott Oake determined as fundraising for women's addictions treatment facility enters home stretch

Melissa Martin 4 minute read Preview

Retired sportscaster Scott Oake determined as fundraising for women's addictions treatment facility enters home stretch

Melissa Martin 4 minute read Thursday, Sep. 10, 2026

For now, the patch of land just east of the Victoria Hospital doesn’t look like much: just a field of rocks, mounded dirt, and concrete piles driven into the earth. Yet when Scott Oake looks over the site, he can already imagine how it will look in just over a year’s time, when the new Anne Oake Family Recovery Centre is expected to open.

It’s easier to picture this time around. In 2020, when the recently-retired CBC sportscaster and his late wife, Anne, were building their first labour of intermingled grief and love, the Bruce Oake Recovery Centre for men, it was hard for him to wrap his mind around how a raw construction site could transform into a welcoming addictions treatment facility.

When that centre opened in 2021, Oake found it looked “almost identical” to the architect’s renderings. So it’s easy to hope the Anne Oake Centre will be the same. It will be the first facility of its kind, its founders believe, not only in Canada but in North America: a place where 50 to 70 women can pursue sobriety while staying with their children.

“At Bruce Oake there’s a culture of love, and most of all a culture of hope,” Oake said, speaking at the site Thursday after a media conference to announce the final push of the centre’s fundraising campaign. “I can feel it every time I walk into that building. And I know it will be the same here.”

Read
Thursday, Sep. 10, 2026

Fallis’s comic thriller infiltrates book club

Ben Sigurdson 3 minute read Preview

Fallis’s comic thriller infiltrates book club

Ben Sigurdson 3 minute read Yesterday at 6:00 AM CDT

The Free Press Book Club and McNally Robinson Booksellers are pleased to welcome Toronto author Terry Fallis to the next virtual meeting on Tuesday, September 29 at 7 p.m. to read from and discuss his novel The Marionette.

Fallis, a former lawyer, bureaucrat and political consultant, is the author of 10 bestselling novels and the two-time winner of the Stephen Leacock Medal for Humour (in 2015 for No Relation and in 2008 for The Best Laid Plans, which also won CBC’s Canada Reads in 2011).

His 11th novel, An End In Itself, will be published in November by McClelland & Stewart, who also published The Marionette in October 2025 (and which was also longlisted for the Leacock medal).

The Marionette follows James Norval, bestselling author of a series of thrillers featuring fictional CIA agent Hunter Chase. While in Tajikistan researching his next Hunter Chase novel, Norval is detained by local officials and subsequently freed and ferried away by the Canadian Security Intelligence Service (CSIS).

Read
Yesterday at 6:00 AM CDT

Threesome’s a crowd

Miss Lonelyhearts 2 minute read Monday, Jun. 13, 2016

Dear Miss Lonelyhearts: I just met a cute older guy online, and he asked me out on a date. He asked if he could bring a female friend, and I joked, "Are you that scared of me?" He brought a friend all right, and they were looking for a threesome. I burst out laughing nervously and walked out. When I said in my profile that I like lots of people and have a lot of female friends, I didn't mean I wanted to play games with them in bed. What a nervy thing to bring her along! I didn't say much, and just left. Was that the right thing to do?

— Three's A Crowd, Transcona

 

Dear Three's a Crowd: They probably had a big laugh. I doubt they were shocked or upset. It was a nervy chance to take, and they knew it. But why didn't you catch on when this guy asked if he could bring a woman? That was a pretty big hint, and 19 out of 20 women would have said, "I'm not going to meet you now." Did you really think he was kidding? Or were you intrigued?

Child hospitalized after being hit in Walmart parking lot

1 minute read Yesterday at 3:46 PM CDT

Police are investigating after a child was struck by a vehicle in a Walmart parking lot on Kenaston Boulevard Friday evening.

At 9 p.m. officers from the Winnipeg Police Service traffic division attended to a motor vehicle-pedestrian collision in the 1600 block of Kenaston, police said Saturday.

A school-aged child was taken to hospital in unstable condition, police said, but the child was later upgraded to stable condition.

Police said the child sustained minor injuries and an investigation is ongoing.

City to hire consultant to analyze 911 staffing levels amid skyrocketing calls

Joyanne Pursaga 4 minute read Preview

City to hire consultant to analyze 911 staffing levels amid skyrocketing calls

Joyanne Pursaga 4 minute read Friday, Sep. 11, 2026

The Winnipeg Fire Paramedic Service is ordering a detailed analysis of its 911 communications staffing level to cope with a surge in emergency calls and the demands of new technology.

WFPS emergency communications staff handled calls for 136,198 separate incidents in 2025. That number has risen every year since at least 2020, when 104,250 incidents were reported, the service’s annual report notes.

The total number of calls to the centre reached almost 275,000 last year. That broader figure also includes multiple calls per event and administrative calls.

“Things have changed in the last decade and call volumes have increased dramatically. That puts pressure on our systems,” said Coun. Vivian Santos (Point Douglas).

Read
Friday, Sep. 11, 2026

A life's story: ‘Ivor the Driver’ found his calling in the ranching life

Aaron Epp 6 minute read Preview

A life's story: ‘Ivor the Driver’ found his calling in the ranching life

Aaron Epp 6 minute read Updated: Yesterday at 9:59 AM CDT

Ivor Asham’s family couldn’t have picked a better image to accompany his obituary. There he is, riding Flash, his beloved brown and white quarter horse, a black cowboy hat on his head and a drink in his hand.

Asham owned and operated Birds Hill Park Ranch for nearly 35 years, where he shared his lifelong passion for horses with thousands of visitors. He moved hay, harnessed horses and drove the wagons, introducing himself as “Ivor the Driver.”

Over the years, Asham built a reputation as the quintessential cowboy.

There’s a restaurant at the ranch filled with memorabilia that he collected over the years. Calgary Stampede posters, cowboy boot-shaped shot glasses, a child’s rocking horse, a wagon wheel and numerous photos of legendary actor John Wayne are just some of the items that line the walls.

Read
Updated: Yesterday at 9:59 AM CDT