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Then he robs you again, then you pickpocket him again, then he robs you again, then...
And you repeat this for 12 hours to train your pick pocketing skill! Exciting open-world emergent gameplay!
There's no pickpocket skill in Oblivion.
Also, when someone acknowledges that you have picked their pocket, or at least tried, you can never pick their pocket again.
kingofthenothing was raised up on the hard streets of Cyrodil. He knows the score.
Nothing sadder than an apathetic highwayman.
"You see, theese ees fiat currency. Thee seestem will begeen to crumble any day now. Ask mee about buulion options!"