‘Tis the season to dabble in costumes

Advertisement

Advertise with us

DEAR MISS LONELYHEARTS: I’m dating a wonderful woman who has turned out to have a totally different style, sexually, than expected. She dresses conservatively for work, but she’s wild underneath and wants to dress up and have crazy sex with me.

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 28/10/2021 (1801 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I’m dating a wonderful woman who has turned out to have a totally different style, sexually, than expected. She dresses conservatively for work, but she’s wild underneath and wants to dress up and have crazy sex with me.

I’ve spent my entire adult life having regular romantic sex, and enjoying it. I’m not saying I’m a man without passion, but I’m not the kind who wants to wear handcuffs.

She has a very dominant streak in her as it turns out. I’m a strong man, but I must admit I’m freaked out imagining what she may want. I have to say she’s 100 per cent wonderful, otherwise — fun, intelligent, loves kids and animals, sports and outdoor adventures.

Will I be able to keep her happy if I tell her I’m not into this sexual stuff? Will she go somewhere else? What do I do?

— Normal Guy, North End

Dear Normal Guy: It’s definitely a problem when you have a great blend of two personalities, but your sexual styles are at odds. If you want to keep this relationship together, you can’t totally reject your new lady’s dominant sexual tastes, no more than she can totally reject your more conservative romantic style.

That means learning to dabble in both, taking it lightly, and learning to laugh when things don’t work out. Can you at least try that?

To take down the anxiety factor for you, suggest a first scene where the submissive revolts partway through the scene, and takes over the dominant role. There’s a little drama that could be fun and exciting for both of you. She may want to dress like a dominatrix sometimes to play games, but know this: Her partner doesn’t have to play the weakling. What kind of challenge would that be?

A lot of the excitement in role-playing for your lady has to do with the exciting costuming. Some of the more expensive lingerie and props can be found at sex shops, of course. But with Halloween coming, you can both find costumes to do with superheroes and heroines or ghosts and monsters. So why not go our shopping together and see what might appeal to both of you?

 

Dear Miss Lonelyhearts: I’m dating an older man (I’m 23 and he’s 31) and my family is really weird about it. My dad is a very defensive “old school” sort of dad. He’s a businessman of some importance in my parents’ rural area, and he told me never to bring “that older guy” around.

We’ve been seeing each other for many months in the city where I live, and I feel like he should have been introduced to my parents by now. They won’t even entertain the idea!

We may be eight years apart in age but we have a connection like I’ve never had before, and he makes me happy. I’d like to marry him down the road and have children with him. He’s already got a solid career and he loves me and respects me and wants kids, too. How can this relationship be wrong?

— Got Unfair Parents, rural Manitoba

Dear Unfair: Your dad thinks an older guy will be after “one thing” from a young woman like you, and not everything else that should go with it — like safety, love, respect and responsibility.

If eight years older in your particular case means your guy is more mature, thoughtful and serious about commitment then Dad might be brought around by a surprise visit.

Since your father doesn’t want a home scene with mom and family present, then perhaps your older guy could arrive alone, dressed well, at Dad’s place of work at quitting time, for a man-to-man talk about your relationship. Now that’s an old-school tactic. Good luck!

 

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

A day on the campaign trail: Winnipeg's mayor, seeking a second term, does double duty

Malak Abas 12 minute read Preview

A day on the campaign trail: Winnipeg's mayor, seeking a second term, does double duty

Malak Abas 12 minute read Updated: Yesterday at 5:56 PM CDT

In the weeks leading up to the civic election, Scott Gillingham has been performing a juggling act: he’s running to be Winnipeg’s 45th mayor, while still serving as its 44th.

“If someone asks me about the campaign, I’m going to answer them. But I think for most people, I’m the mayor of Winnipeg, even if I’m showing up as a candidate,” Gillingham, 58, says. “I try to do all I can to maintain that distinction.”

The Free Press joined Gillingham on a recent rainy September Saturday on the campaign trail, where he served in both roles during an event-laden day. City council’s final meeting before the Oct. 28 election was days earlier.

In Winnipeg, it’s rare for an incumbent to be defeated. But Gillingham knows his win in 2022 wasn’t exactly a landslide — he won with 27.5 per cent of the vote — and he’s been thinking about his second term ever since.

Read
Updated: Yesterday at 5:56 PM CDT

International flavour: Canadian investors may want to make like Ottawa, diversify beyond U.S.

Joel Schlesinger 6 minute read Preview

International flavour: Canadian investors may want to make like Ottawa, diversify beyond U.S.

Joel Schlesinger 6 minute read 2:01 AM CDT

Canada is learning the hard way about the dangers of putting too many eggs in its U.S. economic basket.

Much has been made about the need to diversify our economy away from the United States.

Diversification is understandably beneficial. The more varied streams of revenue a nation has, the less affected the economy will be when one of those sources is interrupted.

The same can be said about investment portfolios.

Read
2:01 AM CDT

Gordon Bell rings in a century

Maggie Macintosh 13 minute read Preview

Gordon Bell rings in a century

Maggie Macintosh 13 minute read Updated: Yesterday at 8:06 PM CDT

Mischka Valencia had gotten used to the hum of heavy machinery at Gordon Bell High School.

“Ever since I’ve been here, it’s all been under construction,” the Grade 12 student said, standing on the sidelines of the brightly painted revamped outdoor basketball court. “I had no idea this was a court.”

The Filipina teenager landed in Winnipeg several months after the inner-city campus had transformed into a construction site.

It was the fall of 2023 and Mischka’s priorities were fitting in, befriending classmates and learning a third language via first-period French.

Read
Updated: Yesterday at 8:06 PM CDT

Mayoral candidate Vogiatzakis criticized for living outside Winnipeg

Malak Abas 3 minute read Preview

Mayoral candidate Vogiatzakis criticized for living outside Winnipeg

Malak Abas 3 minute read Updated: Yesterday at 6:03 PM CDT

A mayoral hopeful took heat from other candidates Friday for living outside Winnipeg while running in the civic election.

Mike Vogiatzakis’s primary residence is in the Rural Municipality of St. Andrews, about 25 kilometres north of Winnipeg — a community with its own mayor and councillors.

But the funeral director said he owns a home in Winnipeg where he divides his time, and he would move to the city full-time if elected mayor.

“It doesn’t matter where a person lives. Why are we dividing St. Andrews and Manitoba and Winnipeg? I’ve met the criteria to run for mayor,” Vogiatzakis said Friday morning.

Read
Updated: Yesterday at 6:03 PM CDT

Sisters relieved hospital takes accountability after mother’s death

Scott Billeck 5 minute read Preview

Sisters relieved hospital takes accountability after mother’s death

Scott Billeck 5 minute read Thursday, Oct. 1, 2026

Eight months after losing their mother, two Winnipeg sisters say an internal hospital review has finally given them something they had been seeking since her death: accountability.

Chelsea Mann and Samantha Burns said St. Boniface Hospital officials acknowledged mistakes were made in the care of their mother, Judy Burns, during a recent meeting to discuss the findings of a critical incident review into her death.

The acknowledgement marked a significant departure from an earlier meeting with hospital officials, when they felt their concerns were largely dismissed.

Burns, 68, died on Jan. 21, three days after being admitted, after experiencing rectal bleeding.

Read
Thursday, Oct. 1, 2026

Puzzles Palace

1 minute read Monday, Jul. 27, 2026

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