Hey, since you work in a service center, the coffee cup holder on my computer broke. Can you help me?

Well, the real ones are sometimes a whole lot funnier than that...
I'll tell you one that, well... wasn't in the tech work but:
I started my professional career as an engineer. One of my first jobs was at a small place in a small town where they manufactured custom heavy hauling rigs and trailers.. BIG stuff, like 100 and 200 ton haulers. It was in the small town near where I grew up, so I knew a lot of the guys there.
I was a rookie, drawing simple stuff, doing load calcs and material calcs, stuff like that... and a whole lot of AutoCad.
The company had JUST switched from drawing on drafting boards and making real blueprints to AutoCad, so it was really new to the guys there... I'm talking like the very day I started is when they were changing over. No one there really knew how to use it very well yet.
"Phil" was the resident eccentric generous in engineering. The guy was still using a slide rule and always mumbled and talked to himself, but he was an absolute materials expert. Smoking was banned in the building, but "Phil" still smoked in the office, they were scared to death that he would quit if he couldn't smoke... and we all took advantage too, we all smoked in there because "Phil" could.
ANYway...
So I'm sitting at my desk and I hear "Phil" mumbling and arguing with himself and I look across the divider and the guy has a RULER, measuring his drawing on the computer screen, trying to figure out the scale and why it wasn't set how he started the drawing. It took me near an hour to explain to him that even though it was zoomed down, the scale was still what he had it set to. He was completely baffled. Remember, these guys were old timers and used to drawing static scale on paper with charcoal.
I dunno, maybe you have to be a CAD user to understand how gut-busting hilarious that was, but we were just about in tears laughing at him and he had no idea why it was so funny.