Eric told me about this site. It's got thousands of designer and tech tales of stupidity. Some will get you laughing out loud.
Here's a sample post:
2 a_j_dalton #1609 | Rating: 4.59
HelpDesk (answering phone): "Help Desk' Client: "What's this funny thing on my computer screen?' HelpDesk: 'What's it look like' (Tapping Sound) Client: 'Dammit, it's right here' HelpDesk: 'Uh... are you tapping your screen?' Client: 'Well, duh!' HelpDesk: 'I can't see your finger over the phone.' Client: 'Well then, how the Hell do you expect to help me?' (sad, but absolutely true)