Full ski week may be too steep for just two of you

Hey there, time traveller!
This article was published 25/10/2025 (338 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I met a bad boy at a ski resort last winter who was on holiday with his friends. We’ve stayed in touch by messaging and phone ever since.

This week he called late at night to ask me if I would like to book a week with him at the same resort after Christmas — on his tab. I love skiing and I’m tempted to go.

Plus, the resort he wants us to visit is in Canada, so I’ll feel safe flying in and out, but what if we don’t like each other as much this season and we’re stuck there a week?

I was with girlfriends last year when I first hooked up with him, so I had them to fall back on when he was busy.

He was great, but he had a girlfriend at home and was cheating on her. Now they’ve broken up, he says.

Should I take the chance? He’s hot and was a lot of fun last year.

— Nervous Ski Bunny, Fort Rouge

Dear Nervous: A week can be a short time if you’re having fun and all goes well, but seven days can drag on forever if the strong attraction isn’t there anymore. Then you may feel awkward with no other friends around — and really find yourselves wanting to go home early.

A “redo” of this type of situation generally doesn’t work well, especially without a social-support system there for you.

In this case, it’s been a whole year since you’ve even seen this guy, and it’s not like you’ve been in super-close contact since then. If it doesn’t go well, seven days could seem endless.

Still want to go? Ask him to consider a long weekend on the slopes together instead.

Dear Miss Lonelyhearts: My new lady friend expects me — a bit of a recluse — to “let go” and accompany her to a Halloween costume party at her friend’s house.

I asked her if I could go in a totally masked costume, and she said I could until midnight. Then the host is allowing guests the choice to take off their masks to mix with each other more naturally. In that case, I told my lady I would like to leave the party at midnight. She laughed and said that wasn’t going to happen.

I’m really hooked on this woman. To do this for her, I’m going to have to indulge in some strong liquid courage at the party.

And, as it gets closer, I’m worrying more and more. Is this maybe the wrong kind of woman for me in the long run — a really outgoing one?

I’m getting really nervous trying to be who she wants. Should I just cancel? How do I even cancel with a woman like her? She’ll try to talk me into it and drag me there if she has to.

— Very Shy Guy, North Kildonan

Dear Shy Guy: If you back out last-minute and leave your new woman to go alone, odds are high that will be your last date, and you really seem to care about her.

Something like a Lone Ranger costume might not be too much of a stretch for you — a cowboy hat, black eye mask you could keep on, plain shirt, star on your chest, cowboy boots and jeans.

You may even source some higher-heeled cowboy boots to help you feel taller and stronger.

This way you won’t be completely hiding away under a full mask and feel exposed at midnight. It likely won’t be a huge issue to keep on a smaller eye mask (and besides, it’s optional).

So why not make it a date to go costume shopping together for some fun and encouragement? It might help you feel better and it may ease you into more of a party mood.

Plus, your new mate will see you’re really trying to make an effort. 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.

Maureen Scurfield
Advice columnist

Maureen Scurfield writes the Miss Lonelyhearts advice column.

   Read full biography