Oh man, I have not laughed this hard in a long time. Here's some of my favorites and you can read dozens more at
http://rinkworks.com/stupid/
I was just talking to a user who had been having problems with her machine -- it was losing its settings every time she turned it on.
Her: "I asked my boyfriend about it. He knows about computers, and he said it sounds like it might need a new sea monster battery."
It took me a while to figure out what she meant. (CMOS battery)
While in art school, where we mostly worked with Amigas and Macs, a Spanish exchange student asked me if I ever worked with MS-2. I thought he meant OS/2 but he didn't know what that was. It took me some time to figure out that he meant MS-DOS. "Dos" in Spanish means "two."
My Teacher: "Do you have a booty disk on hand?"
Me: (almost losing it) "Don't you mean a boot disk?"
My Teacher: "Oh no. I need a booty disk to make the system booty up."
Customer: "I ran Microwave Defrost, but it didn't help."
(Referring to Microsoft Defrag.)
Me: "So, what's your ICQ number?"
Girl: (staring) "Why do you need an icy cucumber?"
A friend had to go over to a bank and set everyone's software up. Since all the Internet software his company supports runs under MS Windows, he asked the manager "Do you have Windows?" The manager stared at him blankly and said, "No, we've got air conditioning."
Customer: "This may sound strange, but my friend told me that if I emptied my cash box, it would help the Internet go faster. Ever heard of that?"
A woman dialed tech support for a large computer manufacturer. She complained that her computer was "eating" her disks.
Tech Support: "Eating your disks?"
Customer: "Well I've inserted over twenty of them and still can't save to the floppy drive."
After a long frustrating call, the customer service representative sent a tech over to the woman's home. He was dumbfounded by what he saw.
One of the front face plates on the case was missing. Inside the computer, at the bottom of the case, were exactly twenty floppy disks in a pile.
Personally when I (sanddrag) worked as a Computer Tech we got a call that a computer was getting a William Randall error. And we are thinking who the heck is William Randall. It turned out to be a Win run.dll error