My husband and I carpool with two other families who live nearby. Our local school isn’t far, but the kids are still too little to walk every day, especially in inclement weather.

Two of the dads, including my husband, travel for work more recently, since it’s post COVID. The third works from home but has early meetings often. One mom is a doctor and sometimes works shifts, so has an ever-changing schedule. I work from home. The other mother doesn’t work.

My problem is that she and her child are always late. They’re never ready when we arrive to pick up, and they show up late when it’s their turn. And I don’t mean two minutes late. Sometimes we’re waiting upwards of 20 minutes in her driveway, or overheating dressed and ready in our hallway.

The doctor mom has said something to the mom who is always late, but it seems to have been ignored. My husband said something to her husband but he’s basically out of the picture since she’s always available. Plus, he said something like, “story of my life….”

We don’t want to stop including them but we and the other family need her to be timelier. What do we do?

Carpool crisis

If everyone’s up for it, why don’t you invite the other two families over on a Saturday night. Feed the kids and stick them in front of a movie, then sit and have an adult dinner. Bring up the topic gently and lightly – this isn’t an intervention.

Your end goal is to continue the carpool, but only if it’s beneficial for everyone involved. Life happens, people’s routines and schedules change, it may have run its course among these three families. That’s OK.

Make it light by keeping it light.

I’m writing to you for advice from across the world. I’m outsourcing so no one will know it’s me. Everyone reads the agony aunts over here, and they’ll recognize the situation immediately.

My boss takes a month off annually to go skiing in the mountains. He’s a widower and his children are all grown and married. He saves up all of his vacation days for this one month away, and we, his employees, keep the business running in his absence.

For the most part, we love and respect him, so we don’t harbour any ill will towards him while he’s gone. However, recently, he’s started doing something that’s very, very annoying. He’ll snap a photo of himself on the chairlift, in the hot tub, at the bar – several in one day – and send them to us with captions like, “hard day at the office,” or “all this work is making me tired,” etc.

Our company runs like any other wherein we all get time off at some point during the year, and many of us travel during those time periods. But none of us rub it in each other’s faces that we’re away, on the beach, or skiing, or whatever, while they’re at home slogging away.

It’s not nice.

How do we tell him to stop text-teasing us, without upsetting him? Let me remind you: he is the boss.

Slightly disgruntled employee

Don’t say anything while he’s away. The best way to get any message across is face-to-face so there’s no misunderstanding or misconstruing of meaning.

And I wouldn’t pounce on him the moment he steps back in the office. But one day, when you’re chatting about whatever, you could gently bring it up. You could say that though you imagine his intention is simply to keep in touch, the photos are having the opposite effect and demoralizing the employees.

Suggest that one photo a week, with a caption of “wish you were here” would have a more positive effect on the group.

FEEDBACK Regarding the kidnapped pyjamas (Feb. 14):

Reader – “Guests misunderstand hospitality when they ‘get really annoyed’ with the host they inconvenience; when they expect that the host bring back the left-behinds; when they use hyperbole like, "why was he holding my pyjamas ransom?"

“Note how the fellow drove the jammies back to the girl, who then slammed him in the press for his delay and frustration.”

Lisi – It seems this column hit a nerve with many of you. I have been on both ends of a similar situation, and yes, it’s frustrating when people leave things behind and expect you to return them. But that wasn’t the case here. She tried endless ways to retrieve her pyjamas and he simply refused to respond. I stand by my comment that his actions were immature and unnecessary.