My most embarrasing so far was just yesterday. There were plenty of pleasure craft fishing and crabbing on Yaquina Bay yesterday and there was a beginning sailing class nearby. The incoming tidal current was as strong as any I've seen on the bay this season and the wind was light and variable. I was basically sailing in place just going side to side against the current and making a little headway.
Well I passed a navigation bouy and thought I had plenty of clearance before I tacked across in front of it. I was so sure I had plenty of clearance that I didn't even look back. Then suddenly the bouy was coming at me fast and I was about to be hit hard directly abeam. I quickly tacked the other way and managed only a glancing blow across the stern to my OB motor and swim ladder. I took some paint off the bouy and bent the ladder platform a little.
I decided to motor down bay and find some more wind so that wouldn't happen again. I was too busy to look, but I'm sure none of the pleasure boats or sailing students missed it.