Essentially, a thief, covered in glass armor (at level 50+), comes up to me, says "Give me all your money", and I answer "[Persuade] Does it look like I have any money" (this is ironic considering I am decked out in enchanted ebony armor w/ dragonbone weapons), "No, I guess you don't, well, get out of here then"

Or something like that. I'm not complaining, considering I get speech experience every time this happens.

On a side note, I really miss how it worked in Oblivion. In oblivion, if a highwayman asked for all your money, and you said, I don't have any, the highwayman would look at your armor stats, if you had equiped less than 100 septims worth of armor, he believed you, if not, he knew you were lying. I really hate how I can be better equipped than any other NPC in the game and claim to be poor.

I usually just exit the dialogue, let the thief attack and then claim the items from their twitching corpse.

I get him near a Nordic Ruin, Iron Bind Burrow I think, one where there are bandits outside. I love killing them, easy gold from their Glass Armor and a unique Mage Hood with no enchantments.

I just tell him to back off, and when he attacks I put him down.