I've never really been satisfied with any games take on handling picking someones pocket, so I developed this method recently which I've used in play a few times now.
Alright, if a thief PC wants to pick a pocket in most cases its just for some random coin and not for targeting a specific NPC. So in most of these regular cases I stipulate that the PC has to be in some sort of group or social situation like a crowded market or tavern. Then I have the PC roll a perception check to case the crowd for the likeliest victim, A success means the thief finds a good target, a failure means the thief doesn't see any good opportunity, a bad failure means that people have noticed the character checking them out and makes further attemps ethier more difficult or even impossible.
Once the PC has found a good mark I roll on the table bellow and give them a description of the target as well as any visible loot. At this point the PC has the option of going through with the steal if they still want, if so they have to make a stealth/dexterity check opposed by the targets perception- If successful the thief gets the item undetected, If not the target could get hostile and things could get messy.
1=Nothing of value
2=Beggars odds and ends
5=Poor odds and ends
10=Commoner odds and ends
15=Middle class odds and ends
18=Highclass odds and ends
In the next post I will explain this table a bit and give several more tables to cover the results.
Part 2: http://therustydagger.blogspot.com/2011/01/picking-pockets-part-second.html