My parents are technically adept, but my extended family is another story.

It took me 2 hours to explain the concept of the internet. He then handed me a floppy disk and actually wanted me to put "the internet" into the 1.44" floppy disk (This was in 2000). A couple of years later I was giving him a website address over the phone, and he was really pissed about the 3 Ws in www.xxx.com.
He argued with me that the world is only one, so there should be only 1 W or something... WTF?!!