Oh mercy me, where to begin?
I think one of my most memorable scenarios involved my imperial assassin. Looking fresh in her shiny new shrouded armour, Min had just finished up her contract to kill betild in dawnstar. The hit went off without a hitch, and after enjoying a couple celebratory bottles of mead over the foreman's quickly cooling body, my girl set off to return to Falkreath to tell Nazir the good news.
About half a mile from town I could spot some quickly increasing figures on the horizon. It was the middle of the night and as dark as Alduins bony butt so it wasn't until they were about 10 feet away that I recognised the Khajit merchants.
And the three wolves.
The caravan bodyguard (I forget their name) was holding sir own, but the rest of the group had made an executive decision to leg it. Feeling oddly charitable, Min lent her daggers to the fight. Which would have been fine if a dragon hadn't chosen to attack.
So Min is now caught between knifing wolves and pinging off arrows at the monster in the sky...which was circling that giants camp nearby. I could hear the dragon land and I shot off an arrow at what I thought was the dragon.
Turns out mammoths are similar shapes in the middle of the night. So it's now Min and the caravan bodyguard versus a dragon and a very peeved giant and its mammoths.
AND THEN ANOTHER FREAKING DRAGON CAME ALONG.
I swear, at that point I just gave up, put the game on pause and went to make myself a cup of tea. That night was worse than when I made the mistake of fast travelling to the rift, only for myself and jenassa to get jumped by a pair of dragons almost immediately. Jenassa didn't survive the encounter unfortunately, but she didn't die in vain. I've never made the mistake of travelling without saving again.
Tl;dr: freaking dragons man.