I worked in ad tech for a while. When the chief creative officer was reviewing designs for a website that included a sign-up form, his feedback was:

Chief Creative Officer: “It should have a checkbox.”

Me: “What should the checkbox be indicating? What text would accompany it? What behavior on the form differs if it’s checked or not?”

Chief Creative Officer: *Condescendingly.* “It’s a little box that, when clicked, a checkmark appears.”

Me: “Yes, I know what it is. I’m asking what the user is confirming when checking it and what happens if they do or don’t check it.”

This $250,000+ salaried executive had no idea what I was asking.

Chief Creative Officer: “Look, forms need checkboxes to look official, so just put one on there!”

A friend and I (both girls) were at a video game store just browsing and hanging out. An employee comes up to us.

Employee: “Do you need help finding anything?”

Me: “No, thank you, we’re just looking.”

Employee: “Have you seen the new Nintendo DS XL’s?”

The Nintendo DS XL has just come out.

Employee: “They’re the best handhelds, and more suitable for games that girls enjoy!”

Friend: “What’s that supposed to mean?”

Employee: “I mean, uh… well…”

Me: *Giving the guy an ‘out’ of this conversation.* “No, thank you. We’ve never been into handheld games.”

Amazingly, despite my giving this dude an easy way out of the conversation, he doubles down.

Employee: “Oh, but they really are very good!”

Me: “I said we’re not interested.”

Employee: “But they have newer, bigger four-inch screens!”

Friend: “You’re not the first guy to try to convince me that four inches is impressive.”

That was the end of his sales pitch.

I worked in software that typically uses two to four large monitors. I’m installing some basic software updates when the user asks:

User: “Can you make it easier to get the mouse arrow thingy to the other screens?”

Me: “We can adjust the Windows settings to accelerate your mouse movement.”

User: “No! I don’t want to have to move the mouse. I just want it to show up on the other screen when I need it.”

Me: “I can make a shortcut key to move the mouse. Control 1 for the first monitor, control 2 for the second, and so on.”

User: “I don’t want to press any keys.”

Me: “How would you like to tell the computer which screen you want the mouse cursor to be on?”

User: *Blank stare for two seconds.* “So you can’t do anything?”

Me: “Sorry, the mind-reading module won’t be released until version 6.66.”

I walk into a corner shop just in time to hear a manager shouting at the young guy working behind the counter:

Manager: “You must like being on the bottom in the bedroom because the only thing you can do is f*** up!” 

The young guy swore back and stormed out, and I totally forgot what I went in there for in the first place…

Before I retired, I travelled a lot for work, about 175,000 miles per year on one major US airline. When I retired, I had flown several million miles with this carrier. With my frequent flyer status, I was nearly always upgraded on international flights.

I went to Japan at least eight times a year for decades and took the same flight over and over. Often, I would wear a white dress shirt and dark pants. Since I flew the same route so much, I knew most of the senior flight attendants and would kill time talking in the galley up front.

On one flight, I had been talking to a flight attendant whom I had known for years about family stuff, vacation plans, retirement, etc. She left the galley, and a younger flight attendant who had been standing with us asked me, as she got ready to block the galley with a beverage cart:

Younger Flight Attendant: “Are you ready to go back to the cockpit?”

Me: “I don’t think that would be a good idea.”

She looked confused and said:

Younger Flight Attendant: “You’re one of the pilots. I see you on this flight all the time.”

She thought I was the captain on the flight, taking a break from the cockpit!

Me: “No, just a really, really good customer.”

She was shocked and embarrassed, but we started laughing.

Actually, variations on this happened several times. On the same route a year before, wearing the same kind of clothes, one of the flight attendants told me they had a new crew member who had never been to Tokyo.

Since we were flying into Haneda, which is right in Tokyo, and the crew’s layover was in Tokyo, not out at Narita, there was actually time to do things.

Flight Attendant: “Would you mind giving the new crew member a one-day itinerary super tour of the highlights of Tokyo?”

So I did, and then asked her:

Me: “What time would you be picked up at the hotel on your departure day? Since the plane leaves in the early evening, you might be able to squeeze in a couple more sites.”

She looked at me like I had lost my mind.

New Crew Member: “You know what time we get picked up, it’s in the crew manifest.”

Me: *Gently.* “No, I am not a member of the crew.”

New Crew Member: *Shocked.* “But aren’t you a pilot?”

The other variation was when a flight attendant would see me board, look at the passenger list ask:

Flight Attendant: “Why are you flying “revenue” instead of “nonrev”?”

Me: “Ah, because I have to pay to be on the flight, since I don’t work for the airline.”

She thought I was a pilot on vacation! You get the idea.