Dear Miss Lonelyhearts: My young neighbour has been hitting on me for years, and to be honest, I’m considering him now.


Dear Miss Lonelyhearts: My young neighbour has been hitting on me for years, and to be honest, I’m considering him now.

I know it’s not behaviour you want to reward, but he’s never been gross. He’s a guy four or five years younger than me, and it’s always been pretty obvious he’s into me, big time.

I’ve always had a long-term boyfriend, but we just broke up, and I’m really thinking about this neighbour now.

My worry is this: What happens if things got weird? What if we had bad sex, and now I’m stuck living next to a guy I don’t want to be in bed with, anymore?

Is it just my animal instincts telling me to find someone for now, or should I really find out what he’s about? — Looking Next Door, River Heights

Dear Looking Next Door: Nowhere in your letter do you say you just realized what a great guy your neighbour is. Your big concern is, what if you had bad sex together and you were stuck living next door?

Basically, you just want to use him, because he’s nearby. Plus, he has a crush on you, so it’s possible you could hurt him emotionally.

Because of COVID, people don’t have the happy option of shopping around safely for a new lover. He may be equally as desperate as you right now, and you could probably get him.

But, it would be heartless of you to give him a sexual whirl and dump him as soon as the COVID threat is over, and you’re able to find someone you really liked.


Dear Miss Lonelyhearts: My best friend is in a scary situation. He’s dating a woman I think is really just in it for his money.

He’s a very successful guy I’ve known since kindergarten, but he has always had a hard time with women. He is just awkward.

Now he has this "trophy wife" type on his arm all the time, and I’m worried she is going to take him for a ride.

Let’s be clear — this woman is very hot, and he is a nerd. Not that there is anything wrong with that, but her vibe is "off," really phoney feeling to me.

Anyway, without getting into more detail, I feel like I need to talk to him and make him see what is really going on. Should I?

How do you talk to your best friend about their partner in a negative way and still remain friends? What if he didn’t want to be around me anymore? — Best Friend for Life, Downtown

Dear Best Friend: Let me tell you a personal story. I had a good friend who fell for a guy who was known to be "very bad news," but she wasn’t seeing it.

I didn’t have the guts to tell her what I’d heard about him, but in the reception line after the wedding, I warned him in a steely voice that her friends would be "expecting" him to treat her right. He snarled back at me.

The final result? He told her what I said, and she never spoke to me again. The marriage didn’t last, and I lost a good friend.

You may feel you have to warn this friend and take the consequences. But, it’s likely he’ll defend the first glamorous woman who has ever paid attention to him and wants to marry him.

Maybe it’s best to let him live his life and just be there for him, if and when he falls.


Dear Miss Lonelyhearts: My five kids are driving me and my wife nuts! They are bored and we’ve done everything with them we can think of, and COVID isn’t over yet.

We’re getting short-tempered — lots of fighting — and the oldest, age 12, was getting the worst of it. He has a temper, like me.

After a bad fight recently, he said he wanted to go and stay with Grandma for a while, and he got his backpack out. It turns out he’d already phoned my mother in the afternoon.

Apparently, she said something like, "Sure. Ask your parents. It’s lonely over here."

My wife got on the phone to her, and I listened in. My sweetie started to cry, saying she felt like a failure of a mother.

Grandma said, "Nonsense. You’re a good mother. Take a break when it’s offered to you!" So, the kid went to Grandma’s three doors down.

Now he’s always coming over here acting like a rock star! He says he wants to stay at Grandma’s longer. What do you think? — Confused Dad, St. Vital

Dear Dad: Let him stay until he gets bored of it, and he probably will as soon as COVID is over and everything loosens up — including you.

Your son has not abandoned your family, by any means. He relaxes, sleeps and eats at Grandma’s; she isn’t lonely anymore and he’s generally a happier guy — feeling like a rock star.

It’s hard to stand out when there’s four younger kids in the family — all needier and getting more attention than you. 


Please send your questions and comments to or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.

Miss Lonelyhearts

Miss Lonelyhearts
Advice Columnist

Each year, the Free Press publishes more than 1,000 letters to Miss Lonelyhearts and her responses to the life and relationship questions that come her way.

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