Get on same page over workplace relationship

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This article was published 21/09/2025 (373 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: Until this summer, I was a selfish workaholic. My second wife left me over this issue recently, just like my first did. I was so shocked I took a month off work to get my head together.

Now I’m back working at my job — a career I love. There’s this woman at work whose breakup story is well-known, and she has kids everybody in the office knows, and I heard through the grapevine this divorced mom had eyes for me. I could hardly believe it, maybe because I was a boring married man for so long.

Anyhow, I finally took notice and last week she came over and we barbecued dinner together. Now I have a huge crush on her. Last night on the phone she told me we’d have to be careful, or “it” will show at work. I admit I don’t know how to deal with being single, and especially having a romantic partner at my workplace. Now what?

— Feeling Lost, St. James

Dear Lost: You need to have “the talk” if you keep dating, although it may seem a bit premature. It’s the “Where’s this going?” conversation. Some couples do very well working in the same place for long periods, but some don’t.

You’ll need to discuss whether the relationship is just about friendship and casual sex or a romance possibly leading to something that could be serious.

A relationship can develop from completely different needs and varying types of attraction for both of you, so it should be discussed.

You must also talk about what your jobs mean to you, and what could happen if one or both of you gets serious over time, and the other does not.

Yes, it seems crazy to have to talk about this stuff now, but it’s important not to get into a situation so uncomfortable one of you has to find a job elsewhere. See the following letter about just such a situation …

Dear Miss Lonelyhearts: I just got a peek of my ex-boyfriend’s new babe. I know exactly who she is because I used to work in the same place myself, not so long ago, and that’s how I met him. I had to quit working there when we broke up, because it was so painful still seeing him every day.

I was not his first in-store girlfriend.

Anyway, I went out thrift shopping today and I’d been browsing at a store I love, that just happens to share a parking lot with my old workplace. My ex-boyfriend still works there.

It was lunchtime, and soon enough came Mr. Hot Shot with some woman. I heard him call her “Babe,” and then they looked my way and quickly got on his motorcycle and took off.

I saw her bright-red hair sticking out from under her helmet. I knew exactly who she was — the annoying 18-year-old he was always complaining about to me, from our work. He used to say she’s “not very bright and talks way too much.” I want to call her up and tell her what she’s getting into with the guy. He’s a piece of work, and treats women like they’re disposable.

— Should I Warn Her? St. Norbert

Dear Warn Her: It’s time for you to rethink this whole scenario, because this ex has obviously moved on — and so should you. Nothing can be gained by spying on him, and it only diminishes you to do so. Instead of dogging his tracks, just disappear from his world and stop thinking about him right now.

September is the best time to join up with new groups and activities, and enjoy the new friendships they will foster. Next time this ex-boyfriend hears chit-chat about you, let it be about something interesting or admirable you’re doing, not about spying on him.

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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