This happened years ago.

In Toronto, there’s a small island airport close to downtown and then the full-on Pearson International. Once every two weeks or so, I’d have to travel for work, so I’d usually book my flight through the island airport since it would be cheaper, and my office was downtown so it took literally fifteen minutes to get there. (There were no real customs or anything; you could show up thirty minutes before your flight departure time and be good to go.) If my flight was at 1:00 pm, I’d leave the office at noon and make it with time to spare. 

One day, I got my expense request denied for the [Rideshare] that took me to the airport because “it was close enough to walk and, as per company policy, taxi/rideshare is only for Pearson.” This was all over $12, and I had been doing this for months.

Okay, fine.

The next flight I booked at Pearson. The ticket was $900 instead of $400, I paid $70 in a [Rideshare] to get there instead of $12, and I had to leave work a full three and a half hours before my flight to make it through check-in, security, etc., to get to my gate in time. Usually, I’d be on some sort of call leading up to my flight, but at Pearson, I couldn’t do any work at all. Sorry, team, I’m unavailable for the rest of the day because of company policy.

When I came by, I was asked why my expense report was double the usual amount I’d put in. It’s because I couldn’t expense a $12 [Rideshare] to the island airport, and I was not going to walk for forty minutes in my suit and dress shoes in the middle of January in the snow.

Two months later, it had cost them over $2,000 more than what I’d normally have spent. Some of the flights in that time were over $1,000 versus $400 at the island airport.

Finally, I got an email one day saying I could take whichever flights I deemed best based on my judgment and that any amount under $700 was auto-approved at the island airport. Now, I get to eat a nice meal and sometimes upgrade myself to premium seats and still fall within budget!

I’m a manager of a restaurant that delivers steak, chicken, and burger meals.

A customer calls in with a complaint that the food they got made them and their partner sick, and they want a refund. After some back and forth, I tell them to give the food back to the driver and their money will be refunded.

They call after a while since the driver hasn’t arrived with the refund yet.

Customer: “Where’s our money? We’ve been waiting a long time.”

Me: “The driver is on the way. He’ll be there shortly.”

Customer: “He’d better. We got pizza coming and need the money to pay for it.”

This was before cell phones were common, so I couldn’t call the driver and tell him to cancel the refund and come back to the store.

When I used to man an outsourced mailroom for a telecom corporation, I occasionally had to open letters to find out to which department they had to go. One occasion was a bit too sweet, to the point of being so naive that I feel worried for this person.

Letter: “I still owe your company €50 for [service]. I have put the money in this envelope.”

And indeed, the money was in there. Baffled, I just put it in the box for the department that seemed right, hoping they would be as honest as I am.

Please, NEVER send cash money by mail to such a big corporation! There is no way of tracking it. Anyone less honest than me might have just pocketed the money and thrown out the letter and you would just have been €50 poorer without any result.

I play cards with a cabbie. He has no shortage of stories about weird passengers. The subject of convenience stores comes up. With the miles he drives and places he has to pick up people, he’s got stories about those, too. He asks us:

Cabbie: “What’s the scariest thing you’ve seen at a convenience store?”

Me: “$4.19 per gallon.”

A customer checks out and buys three candies for a dollar. I start serving the next customer, but then he comes back holding his receipt.

Customer: “Excuse me, but why are two candy bars $0.33 and one $0.34?”

Me: “That’s how they ring up with the deal — three for a dollar.”

Customer: “But they should all be the same price.”

Me: “If they were all $0.33, then it would be $0.99 cents, not a dollar. It’s just how the system counts them when applying the deal.”

Customer: “No! They should all be the same price!”

Me: “What price should they be?”

Customer: “A third of a dollar!”

Me: “Which is what?”

Customer: “Well… it’s…”

He starts doing the mental math as I finish checking out the next customer. The first customer slowly realizes that you can’t evenly split a dollar into even thirds using just pennies.

Customer: “Oh, my God! You should have just told me! I swear I’m not the dumbest person on the planet.”

I’m about to reassure him before the next customer speaks up:

Next Customer: “You’re not the dumbest person on the planet, but you’d sure better hope he doesn’t die.”

I filed that under my list of things I can’t say to customers but wish I could…

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