Santa’s got a special treat in his sack

Advertisement

Advertise with us

Dear Miss Lonelyhearts: I have this crazy, new man in my life and he says he’s coming over to my place on Christmas Eve dressed as Santa and he wants me to be wearing black lace and a Santa hat. Is he crazy or just a lot of fun? I don’t know him well enough to be able to answer that question since we are just eight weeks in. We’ve had some great sex, and I think he’s quite sane.

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 20/12/2017 (3161 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I have this crazy, new man in my life and he says he’s coming over to my place on Christmas Eve dressed as Santa and he wants me to be wearing black lace and a Santa hat. Is he crazy or just a lot of fun? I don’t know him well enough to be able to answer that question since we are just eight weeks in. We’ve had some great sex, and I think he’s quite sane.

Should I indulge his fantasy? He promises he’ll be bringing be a big gift, and I think he means an actual wrapped-up present. I don’t know what would be appropriate to buy him. At this moment, we’re in the beginning stage, but I’m kind of conservative and wonder if I wouldn’t find him sexier in dress clothes. What do you think? — On the Picket Fence, St. Boniface

Dear On the Picket Fence: Get off the pickets, Missy, and have some fun.

And please listen to this: you don’t mess with someone’s fantasy and start reshaping it and making it less. He wants to do this for you (and him!) and you would be a fool to pour cold water on the visualization.

Wear a business suit? Let him plan it all out his way and you take care of the food and drink and the Christmas tree that needs a soft rug close to it.

The bedroom decor should include a fragrant pine garland on the bed or dresser, and candles and mini lights, as you may be spending the end of the night in there.

A plate of cookies and glass of milk (or Baileys) may be required for his arrival, along with a Dear Santa note that’s suggestive!

Try to find out what he hopes will happen and what time he’s arriving, so you know how to play this game. Open the gates to fun and do nothing to inhibit this imaginative fellow you were lucky enough to meet before the holiday season.

 

Dear Miss Lonelyhearts: The kids at my house are demanding toys we can’t afford, and they’re 12 and up, so they know who Santa is.

Should we tell them now, or let them find out on Christmas morning they’re not getting the expensive electronics they want? — Not as Rich as Santa, Windsor Park

Dear Not as Rich as Santa: Don’t start off insulting them by calling them the equivalent of greedy for wanting what they see dangled in front of them.

Just let them know that you have to be a little careful with the money, and you would like to still get them little gifts of love along with some bigger things they would enjoy.

It’s better to tell them now that you wish you could afford those gifts, but you can’t.

Ask if they could please amend their Christmas wish lists so it takes the pressure off and makes it easier for you to enjoy shopping for them. Tell them to make it quick, since Christmas is right around the corner.

Most people — especially young people — understand a budget as they’ve been broke lots of times.

 

Dear Miss Lonelyhearts: Every year, I see this guy at Hanukkah parties and I like him, but he usually has this girlfriend hanging onto him for dear life.

This year, I met him at the first-night gathering of family and friends and he was alone. I sat beside him whenever possible, but he kept disappearing into other rooms and not coming back.

Do you think he was just trying to be sociable and talk to everyone, or was he trying to get away from me? — Couldn’t Nail Him Down, South End

Dear Couldn’t Nail Him Down: I don’t think he’s, er, nailable. If he wanted to get into an intimate chat with you, you gave him ample opportunities.

In the future, if a man at a party makes an excuse or just gets up and leaves you abruptly twice, then he’s not interested. Get that radar working, girlfriend! This guy is definitely a writeoff. He didn’t flirt with you when he had a girlfriend, and he doesn’t have one now and he’s still not flirting. An interested man would show a certain excitement and pleasure in being alone to talk to you at an event.

Don’t overvalue the hard-to-get guys. In a relationship, you want someone who thinks you’re great, not someone who’s cool to you that you have to chase all the time.

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

Sea Bears finish on top

Joshua Frey-Sam 6 minute read Preview

Sea Bears finish on top

Joshua Frey-Sam 6 minute read Yesterday at 8:27 PM CDT

Beauty. Bliss. Ecstasy.

That is how Aug. 15, 2026 will be remembered in Winnipeg.

What was once a pipe dream in the city’s hoops community became an epic reality on Saturday, when Simon Hildebrandt, who grew up playing on the courts of this very town, made good on a three-pointer from the wing to crown the Winnipeg Sea Bears Canadian Elite Basketball League champions.

A storybook ending to a 98-84 victory over the Brampton Honey Badgers sent a CEBL attendance record of 12,519 fans into pandemonium at Canada Life Centre and capped a Finals run for the ages — one that was fraught with injury, impromptu player exits and unprecedented circumstances.

Read
Yesterday at 8:27 PM CDT

Don’t be a big loser — check out Real Love Summer Fest ReunionBig Loser takes the stage at 8:20 p.m. tonight as part of the Real Love Summer Fest Reunion, a one-day event put on by the indie promotion company, which ran the festival in the Interlake area for a decade until last summer’s final edition near Teulon.

Bookers Gil Carroll and Adam Soloway have programmed a full day of music at Blue Note Park (220 Main St.), the outdoor venue adjacent to Times Change(d) High and Lonesome Club.

First up at 4 p.m. is folk-rock songwriter tofusmell, followed at 5 p.m. with a rare performance by indie-songwriting darlings Animal Teeth, a group with several summer fest bills under its belt. Up-and-coming pop-rockers Synthetic Friend take the stage at 6, followed at 7 by the fun electronic dance pop of French Class.

After playing with his full band at last month’s Winnipeg Folk Festival, Amos the Kid will perform a solo set at 8 p.m. Sans band, the performer shows off his affable roots as a Gord Downie acolyte with catchy earworms to match.

Rise of social media reflects rise of self-promotion — to the detriment of genuine storytelling

Reviewed by Matt Henderson 4 minute read Preview

Rise of social media reflects rise of self-promotion — to the detriment of genuine storytelling

Reviewed by Matt Henderson 4 minute read Yesterday at 3:00 AM CDT

A conversation is overheard between two people; one congratulates the other on their success, evident through countless posts on LinkedIn, but the other confesses the prolific aggrandizement is due to slumping success.

A young man on an airplane spends three hours poring over selfies taken on a vacation, zooming in on his biceps and using AI to retouch photos before posting on Instagram.

Anonymous and cowardly trolls on Reddit attempt to end another person’s career.

All this “storytelling” was observed in one day by this reviewer.

Read
Yesterday at 3:00 AM CDT

Poilievre’s lips moving, but Canadians aren’t interested in what he’s saying

Tom Brodbeck 5 minute read Preview

Poilievre’s lips moving, but Canadians aren’t interested in what he’s saying

Tom Brodbeck 5 minute read Thursday, Aug. 6, 2026

Pierre Poilievre’s biggest political challenge right now isn’t Prime Minister Mark Carney’s popularity.

It’s the fact that he still seems to be campaigning against a political landscape that no longer exists.

More than a year after the 2025 federal election, the Conservative leader is still relying on the same message, the same themes and the same attacks that defined his party’s campaign before voters went to the polls.

And Canadians appear to be tuning it out.

Read
Thursday, Aug. 6, 2026

Big Loser’s latest a winning mix of country, folk

Ben Waldman 4 minute read Preview

Big Loser’s latest a winning mix of country, folk

Ben Waldman 4 minute read Yesterday at 6:00 AM CDT

The yellow trucker hat for sale on Facebook Marketplace said “Selkirk Lumber,” so Adam Wayne Brown knew he had to hammer home a deal.

Like the other millennial members of Winnipeg folk-country band Big Loser, the bassist has an affinity for the nostalgic, taking every opportunity — through music, through lyrics and through wardrobe — to recall the unique circumstances of growing up in a changing Interlake.

“I remember the matte yellow trucks driving around — the lumber trucks — and so I’ve had this strange memory of something disappearing from my youth and then persisting,” says Brown, who, like the band’s frontman Alex Paradoski, moved to Winnipeg more than a decade ago.

“I have a photo of the Lockport Bridge in my dining room,” chimes in Paradoski, whose first job as a teenager was bunning wieners and chopping fries at Skinner’s, a drive-in mainstay since 1929 along Highway 44.

Read
Yesterday at 6:00 AM CDT

Santa’s got a special treat in his sack

Miss Lonelyhearts 5 minute read Wednesday, Dec. 20, 2017

Dear Miss Lonelyhearts: I have this crazy, new man in my life and he says he’s coming over to my place on Christmas Eve dressed as Santa and he wants me to be wearing black lace and a Santa hat. Is he crazy or just a lot of fun? I don’t know him well enough to be able to answer that question since we are just eight weeks in. We’ve had some great sex, and I think he’s quite sane.

Should I indulge his fantasy? He promises he’ll be bringing be a big gift, and I think he means an actual wrapped-up present. I don’t know what would be appropriate to buy him. At this moment, we’re in the beginning stage, but I’m kind of conservative and wonder if I wouldn’t find him sexier in dress clothes. What do you think? — On the Picket Fence, St. Boniface

Dear On the Picket Fence: Get off the pickets, Missy, and have some fun.

And please listen to this: you don’t mess with someone’s fantasy and start reshaping it and making it less. He wants to do this for you (and him!) and you would be a fool to pour cold water on the visualization.