So heres the deal, i was walking through riften and as i was passing a guard he said "i dont suppose you would enchant my blade, the thing can bearly cut butter" i just wanted the option to say yes, i would love to help them.

Has anyone else had an exprience like this?

Here's the idea. Raise your pickpocketing to 70, take perk for pickpocketing weapons, pickpocket the weapon, enchant it, and put it back in his inventory. Because that's the only way you'll be able to do it, unfortunately