I lent my brother an OS disc that could boot late last night for a system reinstall, and was curious whether it had worked...the resulting conversation would be "what happens when you don't understand nonliteral expressions and have a sense of humor." ;-)

[02:31] Denise: did the CD boot?
[02:31] Brian: does the pope sh** in the woods?
[02:31] Denise: lol
[02:32] Denise: are you sure your system is set up correctly?
[02:32] Denise: because I know that disc is bootable
[02:32] Brian: it did boot, and the pope does sh** in the woods
[02:32] Denise: oh
[02:32] Denise: I rather thought the pope would sh** in a toilet
[02:33] Brian: nah, woods all the way
[02:33] Brian: he likes the outdoors
[02:33] Denise: lol...likes that special scratch of poison ivy on his ****?

Reminds me a bit of a creative phrase I horrified somebody with online a while back -- "sucks hairy things." As he pointed out, no matter *what* hairy things you're talking about, sucking them doesn't provide very pleasant mental images!