Scholarly guy the smart Valentine’s date, and beyond

Hey there, time traveller!
This article was published 07/02/2024 (970 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I need help with my complicated Valentine’s Day situation. I’m single and dating two men right now, along with a third guy who flies into town occasionally on business. My in-town guys include a brilliant man who is sweet and in his fifth year of university and a guy who’s trying to get himself out of a bad marriage that’s breaking him into pieces.

I’ve never been married, and don’t wish it. I don’t think I want children, but I am not totally sure. It’s not that I don’t like kids, but I grew up poor and ended up raising my younger siblings.

So tell me, how can I celebrate Valentine’s Day in style this year? At the least, I want to go out to dinner with one man or the other.

— Complicated Situation, Osborne Village

Dear Complicated: Dating more than one person can be a headache on Valentine’s Day — but in your case, it’s workable. Let’s look at your three candidates:

First off, Frequent Flyer is out, as he would have to plan a Valentine’s dinner when he’s actually in the vicinity.

Secondly, Married Guy is clearly off-limits for a Feb. 14 public dinner, as he still has a wife.

So that leaves the Perennial Scholar. This man is bright, single and free — with a solid future ahead of him, so good luck with him. He could turn out to be a winner for you yet. Treat him to a wonderful dinner and see what happens.

DEAR MISS LONELYHEARTS: My new boyfriend doesn’t really say he loves me. We’re 33 and 39 and we’ve been dating for almost four months. He only mumbles it into his beard to be polite.

He’s always trying to get me into bed and it works because it’s the only time he comes to life.

I’m afraid if I break up with him there won’t be anyone else. The world seems so small since most of my friends have gotten married, and I was always the bridesmaid. I only have two single girlfriends left.

— Lonely Lady, St. Vital

Dear Lonely Lady: You already know the relationship with the bearded boyfriend is not taking off, so why are you hanging in there? Set yourself free and go travelling with a girlfriend. There’s a month or two yet of great sunshine trips. The sunlight itself will pick up your mood quickly, and the new experiences will make you feel more confident.

Give yourself the gift of a beach renewal and when you get home feeling stronger and happier, consider doing some research online into local activities-based singles groups. You could also look into joining general groups for social, recreational or creative pursuits that interest you, or even explore opportunities to volunteer that can facilitate connections with passionate, like-minded people.

Visit volunteermanitoba.ca to find out about opportunities.

DEAR MISS LONELYHEARTS: I’m 16 and in love for real. This is not just a crush. How do I buy a nice card and gift for my Valentine when I’m only working part-time?

— 16 and In Love, Winnipeg

Dear 16 and In Love: With only $5 you can buy a card and a cute gift. Thrift stores have card sections and lots of romantic stuffies.

Write something sweet inside a card — even make up a little poem — and your mate will love your Valentine’s gift.

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