Does anyone have any crazy board questions that you were asked?

When my Operations Sergeant was going for E6, he had aced the questions, answering every one correctly. Before being released back to his section, one of the board members said that he was going to find something to stump him on. He opened up a copy of Stars and Stripes sitting nearby and found a random advertisement flyer from the PX. He said, "what is the sale price being offered for this iron."

It turns out that the Sergeant's wife had been looking at the sales that morning and was excited about how cheap the iron was because he had ruined hers on all the uniforms (back when we ironed our shit). So, he actually knew the answer to that question too. The now very amused board members had a good laugh over this.

To answer your original question, one of the more odd questions was "without looking, are your shoe laces on your right foot crossed in a left-over-right, or right-over-left pattern."

I took a test for OCS and it had 3-4 questions about fishing, I thought it peculiar.

When I was a young e-4 attending my E-5 board, the Battalion CSM asked me with my 1SG sitting at the table next to him, "Is your 1SG soft like a roll of toilet paper or is he a dick?"

My answer, "CSM, 1SG XXXX is a straight up dick!!!" CSM bust out laughing, my 1SG told me to see him after it was all over because we had some additional PT to do (maybe not that kindly), and I maxed the board resulting in a quick promotion to Sgt.