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Ask Lisi: Be honest about why you want to meet with former co-worker

Your friendship may have run its course or you might still have a strong connection. Just be clear about your intentions
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Advice columnist Lisi Tesher

Dear Lisi: Years ago, before COVID, when I worked in an office, I had what everyone referred to as a work wife. Except he was a man. But work husband just didn’t roll off the tongue as easily. We were inseparable when we weren’t doing our separate jobs, and we often worked on issues together.

Our significant others were more than accepting, and really enjoyed each other’s company when we went to events. We even socialized occasionally outside of work, but not excessively.

It seemed to everyone involved that it was very mature and manageable. Our relationship changed during COVID because we barely saw each other, and though we spoke on the phone, Zoom, Teams, or whatever, we weren’t physically together. And then we both left that job and went our separate ways.

It’s several years later and my relationship with my significant other is failing. I heard that he just broke up with his girlfriend — not the same one from back then. I’m tempted to call him up and meet for coffee.

What do you think?

Work widow

I think there’s nothing wrong with coffee, but only if you’re expecting coffee and not anticipating a hot chocolate fudge sundae. In other words, be honest with yourself (first) WHY you want to meet for coffee. Do you miss your friend? Understandable. Do you think there could be something more between you? Perhaps. Do you just need some confidence and morale-boosting from someone you know who used to think you were fabulous? That’s OK, too.

Just be honest with him as to why you want to meet, and then meet. Your friendship and connection may have run its course. You may realize there was always a flame and you both have room to fan it. Or, you may just have a nice coffee with someone great and move on.

Dear Lisi: I recently met a woman and the sparks flew. We have been going strong for more than six months, we’re both early-30s, and we have always been open and honest with each other about what we want out of a relationship. We’ve discussed marriage, children, family, retirement, future and money.

But that’s where things get interesting. She has a good well-paying job, but lives in a stunning downtown condo that she could never afford on her salary. She has fabulous clothing, keeps up her personal maintenance, has a cleaning lady once a week and a dog-walker for her pooch. She lives larger than her paycheck, obviously.

And that’s what’s strange — she hasn’t even mentioned where the “rest” of the money comes from. It’s clear she’s not sharing everything. Thoughts?

Mystery Money

As you stated, you’ve only been together for six months. And you didn’t mention meeting each other’s families. So, though you two are in love and sharing your every thought, she’s holding back. My guess is that her family has money and either she doesn’t feel it’s your place to know YET, or she’s been taught not to mention anything.

Slow down. I know you both said you want children, and yes, your early-30s is a good time to start trying (more importantly for her than you), but I would give yourselves more time to get to know each other. I also think you need to start expanding the introductions to your parents and siblings, which will then put the onus on her to do the same.

I hope the mystery is nothing untoward and you two have a wonderful future together. I also think you may be served with a pre-nup, if things get that far. Don’t take it personally — from your description, this will be a family issue.

FEEDBACK Regarding the lack of manners at a pool party (July 8):

Reader – “Why is anyone really surprised? This is the result of ‘helicopter parenting.’ Kids are NOT taught responsibility, manners or common curtesy. While growing up, whenever they did anything wrong, the parents stepped in.

“I would give one more chance and make it clear: ANY mess the daughters MUST clean up, as it’s their friends. And if it happens again, their friends are no longer welcome, if they can’t act responsibly.

“And everyone must say goodbye when leaving, especially from a POOL party. People (hosts and adult supervisors) need to know that everyone is leaving and that no one is inadvertently left behind. Sad to say but how many people have drowned in family pools when there is even a moment of inattentiveness?”

Lisi – I agree. Pool parties especially need vigilant supervision, even in the form of making sure everyone has left.

Lisi Tesher is an advice columnist for the Star based in Toronto. Send your relationship questions via email: [email protected].