Over 15 years ago, I drove the 2.5 miles from the bar back to my house. Unfortunately along the way I hit a parked car, which moved forward and hit another car. The first thing I remember after that is hearing some guy yell "Oh shit! That was a company car." Even though I was quite drunk, when I heard that I thought "Uh oh that's not good."
Nodded out while going down on my girlfriend. It's weird when you nod and don't expect to. It's even weirder when you snap back to reality only to realize you're between someone's legs. No idea how that was from her perspective. I don't know what I'd think if someone was giving me head, then just stopped and didn't move all of a sudden.
Sneaking off with a company van to pick up dope was pretty dumb. Worked out ok though.
Trying to buy off the street when I was younger and had no idea what I was doing. Only did it a few times with varying results. Probably most ridiculous time was when I drove past this 20ish woman several times and picked her up. She thought I picked her up to fuck or get my dick sucked or something. I made a deal with her that I'd give her money for crack if she could help me get dope. She had me drive down a street, stuck her head out the window and started yelling "Manteca! Manteca!". Ended up working out. At the time it was way out of my element. I probably wouldn't do anything different today, other than maybe getting the crack woman's number. From the 20 or so minutes we had together the two things I learned about her was that she liked crack and cock.
I guess it depends on what you mean by "ridiculous", but the few times I've had where I couldn't find a vein leave me feeling somewhat scummy. Definitely feel like an addict then, having poked myself repeatedly in many places on my body.