Why not give older, wiser selves one more shot?

DEAR MISS LONELYHEARTS: My nervy old girlfriend — the heartbreaker of my younger self — looked me up and came to see me at my work recently. The sudden breakup with her when I was a young guy almost killed me, so I asked her what the heck she wanted with me now.

She said she wanted to apologize for not giving me enough credit when we were younger. Apparently, she didn’t think I was aggressive enough to succeed in business.

I recall from back when we dated that she wanted to be well set up and to have a bunch of kids, so I asked her how that worked out for her. She said financially it’s been good with her children’s dad, but that it wasn’t really a love relationship and it ended recently.

I then asked her a second time what she wanted from me, and she said, “Just one dinner with you like we used to have, and if it isn’t good, I won’t bother you anymore.” I told her I would have to think about it. Lame answer, I know.

So, should I go out with her or am I just asking for trouble?

— Curious But Cautious, downtown

Dear Curious: If you don’t go, you’ll always wonder what might have happened.

Look, there are not enough adventures in most people’s lives, and this may be a chance to have a memorable one, so definitely accept the date.

If it’s boring or somehow painful, leave politely after dessert knowing an old chapter in your life is closed forever. But if it’s good, and you two are both single again and have learned some important love and life lessons, it might be interesting to explore what could happen now — instead of just wondering.

Dear Miss Lonelyhearts: My new neighbour who bought the land next to my property is an older guy, and I’m a divorced woman in my late 30s.

He has been admiring my horses — I had spotted him doing so a couple times from a distance — and now he has asked me if I would like to go for a ride on a horse he owns.

I asked him what his wife would think about that, and he said, “Nothing. I’m old. She trusts me.” I said I would think about it and get back to him. Frankly, I just don’t know what to think here.

— Wanting to Go, West St. Paul

Dear Wanting: Don’t miss out on this generous offer, and don’t jump to the conclusion this must be your neighbour making a pass at you.

You’ve already raised the issue and this fellow has addressed it and acknowledged his wife. So don’t assume the worst and snub your neighbour and this opportunity.

If you’re uncomfortable going alone with him, perhaps a friend of yours — or even his wife — could come along with the two of you to enjoy the ride.

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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