Meet online suitor at neutral holiday destination

Advertisement

Advertise with us

Dear Miss Lonelyhearts: My husband passed away three years ago. I started an online chat with a guy from England on a games website in August. He has a grown son living with him, and a grown daughter who doesn’t. I’m on my own, but have grown kids and several grandkids. This man and I progressed to Facebook and Messenger, got more flirtatious, and in the fall got into sexting and recently having phone sex. Another comfort zone completely exceeded!

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 09/11/2016 (3602 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: My husband passed away three years ago. I started an online chat with a guy from England on a games website in August. He has a grown son living with him, and a grown daughter who doesn’t. I’m on my own, but have grown kids and several grandkids. This man and I progressed to Facebook and Messenger, got more flirtatious, and in the fall got into sexting and recently having phone sex. Another comfort zone completely exceeded!

His birthday was in October, so prior to our phone call, I sent him an eight-second video of me clothed but sitting on the edge of my bed, for him to open on his birthday morning, wishing him a happy birthday. He keeps telling me I’m gorgeous based on my Facebook pictures, so thought I’d send him something more real and current. He loved it! We had a great phone call that afternoon in every way, but after that we were both busy and it ended up being 10 days with only a few short flirty messages back and forth. I had a sense maybe he was ready to quit this whole thing. So we talked.

He said he had been thinking of us and it was getting to the point where he could literally feel me in bed beside him at night. If we only lived about six hours apart he would be on the next plane, he said. But it is a round trip of 24 hours, and then we would want to get together every few weeks, and it wouldn’t be feasible. He still works. I’m retired. He sounded genuinely saddened, yet he said he’s looking into the possibility of joining me on my winter vacation somewhere when I go for a week this winter. What’s going on? Should I let this fizzle? I want a real relationship.

— Second Thoughts, Winnipeg

Dear Second Thoughts: What if he came to visit you in Canada for a week or two and it didn’t work and you were stuck with him? Why not say yes to the holiday — at least you’ll find out what he’s really like. As for a “real relationship,” it couldn’t happen unless you left your family here and moved to England, where he has a job. No, a holiday is better for now since you’re not on each other’s home territory. You could even book separate rooms in the same hotel. If you’re great together, you could bounce between the two hotel rooms. If not, you’re not forced to be together.

Dear Miss Lonelyhearts: I travel a lot for business. I always see the same guy while waiting at the airport here in Winnipeg. It has become a joke. He waves at me and I wave at him. Recently he came over and we talked and had a laugh. He asked if I were married and I said yes (although I’m not) so he wouldn’t hit on me. He said, “Let’s not exchange last names. This is such a small city. We’re probably related.” So I played along.

Every time we meet, he says, “Hi. Are you still married?” I say yes and he sits down and we chat about this and that. Now I’m starting to really like this guy. He has no ring, but that means nothing. He never talks about kids or family.

Today he said, “Hello, darling. Are you still married?” and I said, “No, I never was. I just say that so I don’t get hit on in airports.” Then I asked if he was married, and after a moment of silence said he was. “Yes, with kids. Too bad, eh?” And to my embarrassment, some tears ran out of my eyes. Now what?

Unexpected Hurt, Winnipeg

Dear Unexpected Hurt: Games can be hurtful, even when they seem protective at first. You’re going to have to forget him, and it wouldn’t be a bad idea to tell him you are done with flirting, to find out his last name, to ask about the reality of his family life and even see some photos of his wife and kids. Each real answer and photo will pour much-needed cold water over your head. Ouch! His poor wife!

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

Today’s horoscope

Georgia Nicols 4 minute read Preview

Today’s horoscope

Georgia Nicols 4 minute read Yesterday at 2:01 AM CDT

MOON ALERT: After 12:15 a.m., there are no restrictions to shopping or important decisions today. The moon is in Capricorn.

ARIES (March 21-April 19)

This is a tricky day. Don’t be too ambitious. It’s totally OK to kick back and relax. But be aware that communications with parents and authority figures might be confused, vague or subject to misunderstandings. Nevertheless, romance is sweet and cosy!

TAURUS (April 20-May 20)

Read
Yesterday at 2:01 AM CDT

Steinbach Credit Union member warns others after scammer steals $10K

Scott Billeck 5 minute read Preview

Steinbach Credit Union member warns others after scammer steals $10K

Scott Billeck 5 minute read Friday, Sep. 18, 2026

A Winnipeg single mother whose bank account was drained of nearly $10,000 says Steinbach Credit Union needs to warn its members about what she believes is a broader security problem.

The woman, who is not being named to protect her identity, said a scammer gained access to her account earlier this week after calling SCU’s contact centre, claiming to be her and successfully completing the credit union’s authentication process.

She said she knows of at least six others who have experienced similar incidents in which callers impersonate SCU account holders and pass the authentication checks.

The woman discovered something was wrong when her minor son asked why money had been transferred out of an account they jointly hold.

Read
Friday, Sep. 18, 2026

Gillingham in lead with decided voters

Nicole Buffie 6 minute read Preview

Gillingham in lead with decided voters

Nicole Buffie 6 minute read Friday, Sep. 18, 2026

A cloud of uncertainty is hanging over Winnipeg as October’s municipal election nears.

Three months after a poll showed more than 40 per cent of Winnipeggers wanted to see someone other than current mayor Scott Gillingham elected, a new Abacus Data poll indicates more than half of Winnipeg voters are undecided heading into next month’s civic election.

Of decided voters, 55 per cent favour Gillingham compared to 23 per cent for former councillor and provincial cabinet minister Kevin Klein and 11 per cent for funeral director Mike Vogiatzakis.

Of all respondents, just over 50 per cent said they were unsure while 13 per cent said they will not vote.

Read
Friday, Sep. 18, 2026

Puzzles Palace

1 minute read Monday, Jul. 27, 2026

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

Give-and-take relationship of Roman leaders takes centre stage in Harris’s historical fiction

Reviewed by Kathryne Cardwell 4 minute read Preview

Give-and-take relationship of Roman leaders takes centre stage in Harris’s historical fiction

Reviewed by Kathryne Cardwell 4 minute read Yesterday at 2:01 AM CDT

British novelist Robert Harris’s latest work is a reflection on tyranny, corruption and betrayal among all-powerful political leaders.

You might be forgiven for thinking it’s a contemporary thriller — it’s actually historical fiction set in ancient Rome.

A former BBC journalist, Harris debuted as a novelist in 1992 with Fatherland, an alternative history where Nazi Germany won the Second World War.

Since then, the prolific author has become best-known for his works of historical fiction, especially his ancient Rome trilogy released from 2006-2015 and the novel Conclave, which was published in 2016 and was made into the film of the same name in 2024.

Read
Yesterday at 2:01 AM CDT

Elmwood–East Kildonan candidate promises to tackle ‘inefficiency’ in government

Gabrielle Piché 2 minute read Preview

Elmwood–East Kildonan candidate promises to tackle ‘inefficiency’ in government

Gabrielle Piché 2 minute read Yesterday at 6:17 PM CDT

The former assistant of late Elmwood–East Kildonan councillor Jason Schreyer is again running for the seat.

Chris Sweryda officially launched his campaign Saturday. He did so with the backdrop of a grocery program he runs, where food is sold near-cost out of St. Gerard School’s gym.

Rows of cereal, pasta sauce and chips filled tables ahead of the program’s afternoon opening. Sweryda created the pop-up with Schreyer months ahead of the former councillor’s April 2025 death.

The program sees roughly 500 people each day it’s open (which is every other week on Saturday), Sweryda said.

Read
Yesterday at 6:17 PM CDT