Hey there, time traveller!
This article was published 11/04/2023 (1265 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I spotted an old love walking down the sidewalk, which was slippery with half-melted ice. So, I said in my best fake British accent, “May I carry you over the puddle to safety, fair lady?” She looked up and saw me, and laughed.

She refused my offer, but I easily talked her into going for a drink, and we hit a nearby bar and had a great time together for several hours. She was flirting like crazy with me — and quite sexual. I thought we might end up together again — maybe that night.

When I asked her to come home with me, she sat up straight and said primly. “Oh no, not happening! I’m getting married in a few months.” You have to wonder what her guy is getting into! Why would she flirt like that with me with double entendres and sexy allusions to our experiences in the past?

As for why we broke up, I was a problem when I knew her, but I grew up after she broke my heart. Help me understand why she did this.

— Feeling Messed With, Crescentwood

Dear Messed With: Maybe you broke her heart way-back-when, but when she was suddenly faced with you again, the old attraction reared up, and she lost control.

Asking her to “be” with you, at the end of the drink was absolutely the right thing to do. You needed to find out if she was flirting and just playing with you — but not available anymore. Ouch! Some lost loves have that effect and there’s nothing you can do except walk away.

Dear Miss Lonelyhearts: I’m a single-again guy in my late 50s and I’m starting to date, but I feel really awkward about where I live. I bought a house many years ago when they were cheap — like $30,000.

I’ve never made a lot of money, but I am usually pretty good about saving and not going into debt. I had some living-together situations with women over the years, but no marriage. Now that I’m older, I think I’d enjoy a real marriage.

With the cost of living rising, I’ve found myself falling behind on house repairs, whether I can’t afford the materials or it’s something I’m not qualified to do, like electrical stuff. My house is definitely at a stage where, if it doesn’t get some money poured into it soon, it will become totally worthless.

I can’t afford to dump money into it, and if I sell it, I won’t get enough to continue living in a house, since it will need some serious work for the buyer. I’m wincing at the idea of moving into an apartment, but it looks like I’m running out of options.

Who wants to date a guy in his 50s who can’t even afford to live in a house anymore? I’ll be alone forever.

— Owner of a Very Old House, West End

Dear Worried: Don’t look down your nose at apartments. They can be better options than old homes that need a lot of expensive work. Also, many women around your age enjoy being able to go out with their man, and enjoy life, so having a bit of disposable income can facilitate dating.

An apartment is not necessarily a turn-off to a woman, if it’s big enough, well-kept and airy. If she’s in her 40s or 50s and her children are gone, she may be living in an apartment or condo herself. For many women, apartment living would beat helping her companion hammer nails, fix pipes and paint his old house.

A nicely decorated medium-sized one-bedroom apartment, with a view of the city and morning or evening sunlight could be romantic — even more so if it has a pool. Also, many apartments now have small gyms and great parking options. In Winnipeg, underground parking can be sexy!

PS: Also consider renting a little cabin at a lake this summer which would be attractive to a prospective partner. April is a big month for booking, but May would be starting to get late for many good options.

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