In 1995, our small internet company called on a potential newspaper client, The Tuscaloosa Times.

Me: (Talking with a publishers exec. assistant) Is your newspaper being published on the World-Wide Web?

Client: I'm not sure but if it is, I doubt it's world-wide.

Client: I want this site to go viral! Do what you need to do for it to go viral!

Me: This is an intranet portal intended to be seen by approximately 25 people. Why do you want it to be viral?

Client: ...Okay, I actually don't know what "viral" means. I heard someone at lunch talking about viral sites and thought it sounded cool. 

That's a pretty big misunderstanding - but we know you've encountered worse ones. 

A hotel chef asked me to photograph some plates of food. I had a rostrum set-up for photographing the plate of food from above against a white background with no cutlery/crockery - as requested by the chef. Then I sent the prints off to the client.

Two days later, I get the head chef screaming on the phone at me.

Client: These photographs are rubbish!

Me: What’s wrong with them?

Client: You have photographed all the dishes upside down!

Me: Rotate the print by 180 degrees and they will be the right way up.

There was quite the silence before he hung up. 

An upside-down story from the Clients From Hell archives!

Client: We have decided we want to call our new website ’_________.com’

Me: Unfortunately, the .com is already registered and in use. However, .net is available. That’s probably the best option unless you choose another name.

Client: Ah. Yeah, I don’t like the .net so much. I think I’ll just stick with the .com

Me: Sorry, I think you must have misunderstood, the .com is already owned by someone else. You need to pick another name.

Client: Thanks for the advice, we’ve decided we don’t like the .net so we’ll just go for the .com as originally planned. If you can register that for us ASAP and let us know once it’s done that’d be great.

A SMH moment from the Clients From Hell archives!

Client: Can you do this design as a painted illustration?

Me: I have a few tricks to make a photo look like a painting, but no, I don't paint.

Client: I thought you were a designer!

Me: I am, but I'm not an illustrator.

Client: There's a difference? 

Two start-up bros contacted me seeking a technical writer. When they explained the loan proposals they wanted me to write, this conversation ensued: 

Me: Based on what you’re telling me, it sounds like you’re looking for a proposal writer.

Client: Yeah, we didn’t want to pay THAT much.

Me: So why are you searching for a technical writer?

Client: Because we’re a TECH company! DUH!

Client: You sent us the wrong format. You gave us a JPG but we need JPEG.

A bit of idiocy from the Clients From Hell archives! 

Client: These photos don't look quite right.

Me: Oh, these are the raw files. I'm going to fix them up a bit in Photoshop.

Client: Which photo shop do you use?

Me: Um... Adobe?

Client: Do they deliver?

This was in 2019. 

I used to be a software developer who also did technical support for a highly niche market (churches).  After several minutes of going through the application with one of the church ladies, we get to this point in the conversation:

Me: Ok, now use the left arrow key to go to the beginning of the line.

Client: You mean the Enter key?

Me: No, ma'am, the left arrow key?

Client: You mean the Backspace key?

Me: No, ma'am, the left arrow key.

Client: I don't have a left arrow key.

Me: You don't have a left arrow key?  Do you see the Enter key?

Client: Yes

Me: Now move your finger down one row, and over to the right a little bit and you should see four arrow keys.

Client: Oh, you mean the left arrow key!