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Frankly, I'm not really sure I want to roleplay with you at all. Every previous thing we've tried has failed, miserably, and I think our styles and interests don't really mesh well.
Nightmare Moon is equally "Aahaahaaaawww I'm evil!" Until she becomes Luna, and Chrysalis... Might work, but if I'm being honest here all the MLP big bad villains are kinda boring once they reveal themselves, except for Discord. And he's not someone I'd want to roleplay about either.
Merry Christmas to you, too!
But I'm going to have to turn down that idea. Sombra is, as far as MLP characters go, one of the most featureless and bland villains ever. He's got no personality beyond "Evil" and maybe "Likes crystals".