Why not throw Hail Mary for your old love?

Hey there, time traveller!
This article was published 05/09/2025 (346 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I went to a school reunion this summer and it sucked because I was too chicken to ask my old love out. I’ve been dying to contact her ever since. She looked so amazing and sounded even better at the different get-togethers.

In the end we talked for two hours straight and ignored everybody else. Then we went out in the field behind the school — the place where we had once kissed and said “I love you” after my team won the football final. I was a big hero in those days.

I know where she works and where she lives now, but she told me in a regretful tone at the reunion that she had a boyfriend, though she added that he was not a keeper.

I didn’t respond because I was too choked to say, “Phone me when you punt that loser.” My heart was beating out of my chest.

She scribbled her contact info on my reunion program. Was she giving me a hint before she left? Should I call her, now that more than a month has passed? She’s likely still with the boyfriend. What if I get shot down?

— Itching to Call First Love, Charleswood

Dear Itching: Don’t let fear of a possible “No, thanks” get in the way of a possible “Yes, I’d love to see you.”

Your chances seem pretty good here — she did give you an obvious hint. So, call her before she lets Mr. Just OK go and finds someone else who is once again, not you, because you didn’t seem that interested — again. Your heart may have been beating hard, but you didn’t take her hint in the field at the reunion.

So phone her today at any hour you have the courage. If she wants to see you, she’ll be excited to hear your voice.

Dear Miss Lonelyhearts: I’m a bisexual woman and my new boyfriend is letting that fact get in his way. I’m serious about getting serious with him, but he’s worried I’ll get bored and maybe want to see another woman at the same time, like it’s a treat.

I understand his worry to a degree, but I would love him the most.

Still, I wouldn’t want to be deprived of having another woman for my whole life. So what now?

— Bi-Woman’s Problem, Winnipeg

Dear Problem: For now, you might consider enjoying your time together, knowing it’s likely not going to end up in marriage. Then, let go of each other as gracefully as possible when the time comes. Just don’t chop off the relationship prematurely.

Give it a long enough run that you’re getting weary of the limitations or, despite your current expectations, he surprises you and becomes more comfortable with what you may need.

In time, you will probably both want to be free, to find someone totally suitable. Sadly, you can’t guarantee you’ll both want your freedom at the same time.

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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