I found this site that has a large collection of stories and anecdotes about clueless computer users.
Here's one of my favourites..
My friend called me up one night and asked me to help him with a problem he was having sending email.
- Friend: "I can't send any email to you."
- Me: "So what's the problem? Are you getting any error messages?"
- Friend: "No, but everytime I try to go to your email it asks me for your password, and you never gave it to me!"
It turned out he was trying to get into my Hotmail account to send me an email.