Proper caution, timing required when asking date’s mother out

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This article was published 02/04/2026 (200 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I thought I had fallen for a younger woman, until I met her mother, who is only in her late 30s.

She got pregnant in her late teens and kept the child. When I met her, her daughter and I had only just met and had a couple of dates, but had not had sex yet.

I drove out to their farm for a group dinner of friends and was seated next to my date’s mom, who was clever, witty and young-looking for her age. I got all her off-the-wall jokes, and we were both in stitches.

I left the party feeling very confused. I was more attracted to the mother than the daughter.

The next day I got a phone call from the daughter, who told me she was sorry she couldn’t see me anymore because her ex-boyfriend had heard about me and was jealous. Apparently, they talked for hours and actually made up. I guess I’m good for something.

Apparently, they’re in love again and the relationship is seriously back on. I actually heaved a sigh of relief.

Since the dinner party I had been thinking about her delightful mother. Is it wrong to want her? She’s closer to my age, after all. If it’s just about the timing, I can wait. What do you think?

— Willing to Wait, rural Manitoba

Dear Willing: There are two important things to be very careful about here.

First is the timing, and the second, more importantly, is preserving the mother-daughter relationship. You can’t risk damaging that or it will haunt your romantic relationship forever.

So, if you do happen to hit it off with the mom, be discreet when going on dates try to avoid public displays of affection.

Even if the daughter is back with her boyfriend in a serious way, you need to take the relationship with the mother very slowly. Someday you and this more mature woman may look back and laugh about the way you cautiously got together, but not just yet.

Dear Miss Lonelyhearts: My ex moved back to the city and I can just feel her annoying presence here from three neighbourhoods away.

After we split up and she left town, I continued with the clubs we had both belonged to, improved my tennis game and made some great new friends.

I have my eye on someone special in one club right now and I hate seeing my ex’s face back on my turf. She swore she’d never come back to “small-town Winnipeg” but I guess she couldn’t make it in a different city. So now what?

— Wish She’d Go Away Again, Whyte Ridge

Dear Wish She’d Go: Instead of avoiding your ex, face her. Ask her (nicely) why she came back. You might be surprised at her answer. Maybe she appreciated her old friendships in Winnipeg, felt lonely and missed living here. It’s a great city when you know how to enjoy it.

Obviously, she also likes this old club you both belonged to, and maybe was hoping enough time had passed that you two could call a truce and still frequent the place.

Hopefully she’s willing to give you space at the club, and you could graciously grant her the same.

Who knows? You may find out you both like each other again — or not.

Dear Miss Lonelyhearts: How long do you have to wait before you make a move on somebody you only see in class? I’m crazy about this girl I see in one of my high school classes and in the hallways, but I never have the nerve to say anything to her.

Last week she smiled at me and said hi, and I was so shocked I ducked my head and almost ran into a locker. To make things worse, my voice is changing and I’m afraid if I said hi to her my voice would come out like a squawk. Please help.

— Shy Guy, Winnipeg

Dear Shy Guy: Since you can’t trust your voice to respond to the girl you like without cracking, just raise your hand in a casual salute and smile at her. She’ll probably think that’s cute, and won’t care if you don’t speak. She might even stop and talk to you to make a smart crack about the salute. Any excuse to communicate will do in the beginning, so best of 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.

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