Be upfront for smooth sailing with old roomie

Hey there, time traveller!
This article was published 22/09/2022 (1462 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: My former college roommate and I reconnected online recently. She’s a young widow who lives in Toronto, and I’m recently divorced.

The big news this week is that she’s invited me to join her on a cruise this coming winter. She was always a ton of fun, but I’m afraid it will bring back memories of her honeymoon, which took place on a Caribbean cruise. Would I be stupid to take that chance?

— Carefully Considering It, Fort Garry

Dear Considering: It depends on how long ago she lost her husband, and whether or not she’s still in mourning for him.

If she’s over the worst of it, and you cruise in different part of the world than her honeymoon, it could be a fun experience for both of you.

The bigger question is how you two relate now, as grown-up friends. Can you afford to have your own cabins, so you aren’t in each others’ space all the time, or snoring and keeping the other one awake?

Also, be aware that one or both of you might want some privacy if you meet a sweetheart on the cruise. What will be the prior agreement about handling that? As grown-ups, you need a plan!

If you ask all the right questions and sort things ahead of time, it could be a great experience. But, if you don’t talk about it first and just go on the trip hoping for the best, you could hit choppy water.

By the way, COVID is still a concern, so make sure you investigate that situation beforehand, and what would happen if you, or the whole boat, end up sick.

Dear Miss Lonelyhearts: My heart has been broken since my wonderful brother-in-law moved out of town. I was in love with the man, and I know my sister sensed it, and hated it. Not that he loved me back!

I just couldn’t leave him alone. I was always over at their house asking him to show me how to do things — or inviting him over to fix something at my place. He’d never come over without her or a buddy though.

I’d flirt with him, and he knew it. Nothing sexual happened but after a while, my sister wouldn’t let us be together anymore. She was always the beautiful and smart one. She decided to put a thousand miles between us!

She put in for a transfer with her company this summer and got it! They just went off to Alberta. He doesn’t have a job yet, but he’s big and strong and skilled, and can get a building job anywhere.

I have no money to visit, and my sister definitely won’t be sending me any tickets. I feel so empty and useless without both of them, and I can’t stop crying.

— Lonely Sister, North End

Dear Lonely Sister: The smartest thing you can do now they’re gone, is get some professional help — either from a psychiatrist covered by provincial health care, or a psychologist, paid for by you or your work insurance plan.

You’ll finally be able to understand what was really happening with you, your sister and her man. With good help, you can start the work of fixing the different facets of your problem.

When you graduate that process you may finally be ready to meet your own partner. You’ll also be able to write your sister, to explain and apologize. Then she may feel free to see you once again when she visits family back in Winnipeg.

When you feel sorted out, you might explore local singles groups and dating apps to meet fun groups of people — and maybe someone really special, just for you.

Dear Miss Lonelyhearts: I just retired early from my stressful job. I moved out to my former country town near a beautiful lake, to get some much-needed rest and relaxation. Who do I run into yesterday, but an old friend from high school, who’s hoping to be mayor of the town one day.

Oh brother. He’s already trying to get me involved in his big projects. I just want to be left the heck alone, to unwind. I don’t want to make an enemy, but how do I tell him to leave me be, until I’m ready, if ever?

— Enough Pressure, rural Manitoba

Dear Pressure: Be cool about this. Small towns are good for relaxing a guy quickly, if he does nothing. You may feel relaxed and rejuvenated more quickly than you expected.

If the word’s out that you don’t want to be bothered with town projects, people are probably not going to “bother” you. So, be wise and ask the person requesting your help to get back to you soon — and take down their phone number, as a show of good faith.

If they don’t come back and you’re finally bored stiff, make sure you reach out and make contact and tell them you’re well-rested and ready to help out.

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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