Extricate yourself from messy father-son debacle

Hey there, time traveller!
This article was published 26/07/2025 (412 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: While my apartment was being renovated, I went to pick up the last of my things from the guy I was living with. I was staying every night in his bed, but it was just a casual thing for me. He was much too young for the relationship to last.

I was delighted to get into my renovated apartment, but I went back one more time to his place to get the last of my things, and guess who opened the door to my recent boyfriend’s place? The older version of him.

This man obviously knew who I was. He said, with a big smile, “My son isn’t home. Why don’t you come in for a drink and we’ll have a little visit? I’ve heard a lot about you.” In the end, we talked for more than two hours.

I should have guessed the “old block” would be even more charming than “the chip.” My ex’s dad was only 20 years old when his son was born, and he’s still an absolute doll in his 40s.

We got along like a house on fire, until he started actually pursuing me sexually in the days that followed.

I never gave in, thank goodness, but my ex-boyfriend found out from his father about our long chat and things almost got violent between them. Now they’re not speaking to one another at all.

To be clear, I never actually slept with his dad. Why doesn’t his son just get over it?

— Ridiculous Fighting, Exchange District

Dear Fighting: It shows serious disdain and cruelty on the father’s part to compete with his son over a young woman he was dating.

The son can never trust his father now. This kind of fighting between father and son over a woman cuts so deeply.

Even though you had already broken up with the son, the father had no business coming on to you, and the son didn’t deserve to find out you actually welcomed the flirtation from his father, at least at first.

If you have any kind of compassion for the son, get the father out of your life in every way.

Then stay far away from both of these men. You are the match that could ignite a very dangerous fire.

Dear Miss Lonelyhearts: I inherited a large amount of money from my parents and invested it. I also have my own career in finance, which pays well, and live happily on a horse farm near the city.

I love my animals more than most humans, and I’m very happy with my staff at the “ranch.” Everybody is well looked after, but recently a sweet man from my work has started trying to make inroads into my life. I did find him attractive at first.

He accompanied me to events when I needed an escort, and we had a nice sexual relationship, as well.

But I recently had to tell him our relationship was definitely not headed for any kind of commitment and certainly not marriage. He was so crushed. Now he’s withdrawn and depressed at work. I hate knowing I hurt him so badly.

Then, just today, I heard he found himself a new job. I am shocked. I don’t know what to say to him, but he deserves more than just a goodbye.

He’ll be gone from work soon. Please help.

— Feeling Guilty, East St. Paul

Dear Feeling Guilty: Write this man a letter to express your feelings and tell him you wish him the best with another woman who is a great life partner and makes him happy.

Don’t mail it, as that would be too impersonal. Ask to see him alone after work and hand him your note.

He probably won’t want you to watch him read it, so don’t stand there waiting. Just give him some privacy to struggle with the note’s contents and his painful emotions.

You know you can’t give him the love and attention he deserves, but that shouldn’t stop a guy from having hope.

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