Not sure if I'd class it as the craziest moment of my life, but it was like a scene out of a sitcom:

When I was a teenager I briefly worked part-time at a place that refurbished various household appliances. Donations came in through the front and ended up in back with very little looking over. We took all sorts in and the workshop floor was split into various departments based on what appliances they dealt with. I was a new hire and they were still cycling me 'round various departments, my least favourite one was when I was assigned to cleaning out used ovens.

One day this box came in and, like, we opened it up and there were various electronic massaging gizmos. So, my supervisor is pulling 'em out, he passes some of 'em to me to give a lookover to make sure they're clean and do, like, PAT tests and stuff.

I'm plodding along and he gets to work on the rest himself. I'm doing the tests on this thing that's like a plastic plate with this piece on the top vaguely shaped like a pair of cupped hands, when my supervisor calls me over to lend a hand. He's got this black tube that goes a bit wider on one end, about as thick as my wrist. It looked kinda like a torch but with a cap screwed over the bit the light's in.

His hands are a bit slippy so he's having a hard time unscrewing the cap, so he asked me to have a go. Wider end pointed away from me, I wrapped my hand around the cap and gave it a good twist. The first clue I had that something was amiss was that my supervisor went bright red. I asked him what's wrong and just told me to see for myself, so I turn the thing in my hand and see this silicone orifice looking back at me.

That was how I learnt what a fleshlight is.

Probably being held at gunpoint by a guard at a Jordanian airbase that I was inside of, doing a timed ruck march, as a US soldier.

I didn't speak his dialect, so I couldn't pick up much, but my gut said he was pissed he was on guard overnight and decided to ruin my night, too.

Only like the initial 15-30 seconds were really stressful, it was largely just annoying, since I couldn't communicate with anyone, standing there with my ruck on the ground and my hands up.