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1.Breton (Manmer)
2.Dark Elves (Dunmer)
3.Wood Elves (Bosmer)
4.Orcs (Orismer)
5.Nord
I've never played as any of the others but I think Imperial and Kahjiit would round up the end, Imperials are boring and too many people play as Kahjiit. XD
When I first got Lydia, I accidentally killed her. Said: "Oh well, she will be missed." and moved on. Now, when my followers die I have to reload. I cant risk losing Uthegerd, Mjoll, or Marcurio for good!
My favorite has to be when you first join the Dark Brotherhood and you hear the little girl Babette:
"(old man voice) Come here, a little sweetie for the sweetie?"
"(Normal voice) Oh yes, how about in that dark alley Mr.?"
"(Old man voice) That sounds delightfull! My, your teeth! They're...
Valenwood and Elsweyr. It's perfect because they're neighbors and the total land area would be about the same size of Skyrim. This could also be where the Empire makes the first attack on the Dominion. :D