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You all have your political reasons for picking but mine was more personal. As a dark elf, I originally wanted to side with the Empire, but then I met my npc fiancé, Jenassa. She was a dark elf too. She fought alongside me against many foes before I tried marrying her. When we tried getting...
*tiny spoiler* near the end of the thieves guild main quest you are given an all black armor that has a cape on it. Makes me feel like Batman when I wear my ebony helmet.