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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
I had to vote for the Thieves guild because I loved how the whole guild was betrayed and my enemy became my ally and we went and killed the sumbxtch. I know that the Dark Brotherhood is similar but like EVERYONE dies so it is kind suckish after it's you, Nazir and a little 300 year old girl...
I have a fourth character now. :D
Wreyn (Pronounced Ren) the Willful (No relation to that dirty priest of Boeithiah xP), Nord, Huntress and Warrior who plans to join the Stormcloak rebellion and regain her home from the faithless Imperials.