How about deciding to take a shortcut over the mountains from Whiterun to Windhelm and running into Shearpoint, and thinking "Hmmm, what's that over there? Ooooo. A word wall! And a dragon! And he's sleeping. Maybe I can sneak up behind him and lay the smack down." and Lydia says, "I've got a bad feeling about this." Why didn't I listen?

There is nothing like dealing with a lich named Krosis who starts flinging fireballs AND a frosty blood dragon at the same time, not to mention the cave bear that decides to turn the entire thing into an even bigger Charlie Foxtrot.

Going through enough healing potions, stamina potions, and magika potions to choke a horse. I'm really glad I wasn't playing on Master level. I barely survived it on Adept. I fortunately knew enough to use my fire shout on the dragon

, and use shock on the undead dragon priest

. Lydia went down for the 9 count at least twice. BTW. Lvl 21. I'm really glad I upgraded to elven armor (flawless) before that -- thank you Khajiit thief.
Then immediately afterward while I was catching my breath, a wolf attacks... Lydia got it with an arrow -- it sounded like a sniper rifle fired -- headshot. I would have been toast with one hit. And on the way into Windhelm, at Ange's Mill I almost was killed by a mudcrab while a Courier was delivering this oh so important message in a conversation I couldn't break out of. Lydia was nowhere to be found. Probably was trying to pick her way down the mountain.
That was my toughest quest so far in the game.---- this playthrough.
Last playthrough... aborted due to bug... You know how sometimes we do stupid things? Like thinking we actually have to be the big game hunter to get the
mammoth tusk for Modesi? Well, I thought I had to kill it. It took an hour. First I had to deal with the giant, and this is where I found out how far a giant can drive the Dovakiin: 300 m. I swear he his shirt said "Bonds" on the back and San Francisco on the front. Reload. Then this time be a tiny bit more intelligent managed to actually draw the mammoth away from the giant I found out how fast they are. But I got one down, and then found out that the giant does try to retrieve his prized possessions and doesn't take too kindly to having Betsy killed. 300 m. Reload. I know what you're thinking. Wiley Coyote. So I opened my Acme Catalog and checked for the latest strategies and now familiar with the terrain figured how to get one of them blocked so I only had to take one at a time, and I ordered some poison. One mammoth down, tusk gone. used whirlwind and ran like hell. Beep! Beep!

This time I just bought the tusk.
