[Jack of Speed]

In my current HoF game(the Caster Heavy One) I have a pure rogue to do the talking for the party but I am also maxing out her pickpocket so I am going to try to pickpocket EVERYONE. Oh and I did something a little weird/cheap to that guy in the Callaway Trade Depot. I "Charmed" him, the spell, and then I could pickpocket as much as I wanted without him turning hostile. BUT the rules say he will remember when he comes out of the spell what happend to him. Does anyone know if he will remember the 347 times I couldn't pickpocket him or will he remember the 1 time I succeeded? Because a succesful pickpocket goes unnoticed and if thats all he remembers then who cares. However I have not been able to test this since he will NOT become "Uncharmed". Dispel magic won't even work. Uh, Eh, Ah. Thoughts?