My most embarassing moment is a little more tame than the "Moon over Bay Lake" story (sorry Bob), but it didn't seem so at the time. It was my first ever visit to the MK, and I was just 15 years old. This was circa 1976.
I was traveling with a group of friends from our local Explorer Post, which was a thinly veiled group of juvenial delinquents that were away from their parents for the first time. We were walking up the ramp to the monorail at the TTC, and the leader of our group, Roy was giving one of his generally hialrious spiels about something. I had my head turned far to the right to listen to him, when BAM!!!, I walked face first into a light post. The combination of my head and my metal framed glasses hitting the post was enough to actually make a loud CLANG that reverberated all over the relatively empty plaza at the TTC.
Immediately, my "friends" all pretended they didn't know me as I stood dazed and slightly bleeding, with hundreds of people rolling on the concrete laughing. Fortunately, I wasn't seriously injured and was able to bend my glasses back into some usable shape.
I think that subsequent updates to the ramps have eliminated the poles in the middle of them, probably due to idiots like me.