I got this message the other day when trying to dismiss an Outlook calendar reminder:

I'm not sure quite what I find funny about this, but here are some reasons:

• The four sentences are very short and staccato.
• It has an almost desperate quality--especially the "You may be reminded again" part. (Oh goodness--not only did it not work, but I might actually be reminded again!)
• It adds "Could not open the item." which must be something it needs to do internally before it can turn off the reminder, but conveys no useful information to me as a user.
• I like that after all this, it hopefully adds "Try again."

Just to be clear, I've written (and continue to write) my fair share of wacky dialog messages. I usually end up writing something like this when I'm almost positive that it will never actually happen, and therefore don't need to spend a lot of time polishing the content. Writing this type of failure message can be a bit difficult and time consuming to do well. However, when one of these pops up, it's pretty amusing!