I made this a wiki because I think that some people may think it's too "thready" but I had to share and it wasn't appropriate on my blog.
I've had a few, but I think the strangest was once I was on an interview (when I was consulting) and it was my first interview. I wasn't 100% familiar with the position, I knew they wanted to utilize my experience with SQL server to import and archive older data.
Well, I was in a man's office, we were alone and he closed the door on the way in. After a few questions he looked at me with a total straight face and said seriously "So, do you have any experience with Wang?"
Those unfamiliar with American slang should google (or not), but I was frozen silent and beet red for about 30 seconds before he said "It was a database machine in the 70s."
I'm sure that other people have funny stories, sometimes we nerds can be awkward.