My worst time being stuck had absolutely nothing to do with overlanding.
My girlfriend at the time lived on a state highway in west-central Ohio. Her family's house was quite a ways back from the highway, and had a looping gravel driveway to get there with some off-camber curves.One winter night, instead of driving my VW Scirocco, I was driving my mother's 1968 Oldsmobile Cutlass Supreme. All these years later, I don't remember why. Maybe we were on a fancy dinner date, or maybe the VW was broken.
I was there until well after 1 AM, and while we were inside, it had snowed about 8" on top of the several inches of snow we already had, and out in the country like that, it drifted a lot. I'm sure you can see where this is headed...
So there I was, very late at night, off the side of the driveway, in over a foot of snow, spinning the wheels trying to gain some traction in a car with no weight on the rear end and wide, useless tires. I'd try to dig some out with my gloved hands, and go at it again. Eventually, my girlfriends' father and brother, who had already gone to bed, came out to help push me out. Very embarrassing, and certainly endeared me to her family.
That's her in the avatar above.