My most embarassing overboard:

I once owned a 30' sailboat with a lot of brightwork. I was a purist then,
no Cetol, I applied coat upon coat of varnish. The yacht was a thing of
real beauty! I would sometimes stop at the marina after work, change
clothes in the boat, and apply varnish. One such day I was working on a
large area of teak and applied masking tape. It took quite a bit of time to
apply the tape and I wasn't finished so I left it on for a couple of days.
One evening rain was forecast so I stopped by the boat to remove the tape
even though I wasn't finished. I had taped completely over a ventilation
cover and when I pulled the tape off all the wasps in the world came out at
me and boy were they angry! I jumped toward the dock, clearing the
lifelines with one foot but not the other. I went overboard. Luckily the
dock was almost empty but I was glad to have help getting out of the
non-floating dock.

The most embarassing I've seen:

While applying a coat of varnish one evening when the boat was in a
different marina, with floating docks I stopped work to watch the Island
Packet across from me come in. This boat was owned by two ladies and let me
tell you their handling that boat was a thing to behold. The were really
good. This day they came in from a day on the water and had a couple of
guys aboard with them. As they approached the slip one of the guys got onto
the bow, grabbed a dockline, and stood there. They boat was already
alongside the dock and stopped, the captain had done her usual great job,
but this guy jumped off the bow holding the bowline, balanced a couple of
seconds with one foot firmly planted in the center of the dock, arms
flailing all about, and then went head first into the empty slip on the
other side of the pier.