Maybe "worst" is strong. Think of it like "most embarassing or awkward"... The most unfortunate time that your gun was exposed and you didn't mean it to be.

Mine was at a local restaurant. Sitting with a group of friends for 'trivia night' there. The chairs there aren't real comfy to start with, 'trivia' takes about 3 hours. I was carrying my small pistol in an IWB holster at about 5:30 position, as is my usual. This normally presents no problem sitting, as my back 'curves in' enough to have a small gun nestle in nicely.

But that night, for 3 hours on an uncomfortable chair, I guess I was squirming and shifting enough - not because of the gun but rather my bottom & hips - to start working the holster up. Normally I'd have noticed it shifting and readjusted it, but I guess the overall discomfort made me not notice it.

The holster is very secure, but over the course of a few hours, eventually the clip worked loose and ka-thump... Gun & holster fall on the floor behind me (open-back chair).

Thankfully, the only reaction was from my friend on the next chair who looked down and said "Oh I feel much safer now"... I just calmly grabbed it and put it back and went on about things.

Only time I've 'dropped' my gun. I did retire the belt I was wearing that night since it had also maybe got a bit too soft for carry duty.

So my 2c is replace your gun belts when necessary and if you squirm a lot, check your piece.