Kingdoms of Amalur: Reckoning

Go to a Fateweaver and rank up your stealth (I maxed out mine just to be safe) You might not have to rank it up at all with my method but I still recommend it just for safety. If you don't want to rank up your stealth then try this method with a potion that gives you more stealth or makes you invisible.

JUST REMEMBER: EACH TIME YOU GET CAUGHT PICKPOCKETING, IT DOESN'T COUNT!

1. When ready, go to GORHART, and into THE CORNER SHOP.
2. Once inside, look to your left for a woman named RIKKA EGEST, behind a counter.
3. Go into stealth mode (Press Right Bumper) and sneak over to the side of her counter.
4. Make sure you are at the side of the counter so that the other two NPC's in the room cannot see you.
5. Sit perfectly still and within a short time everyone should lose complete track of you (watch the eye meters).
6. Now even with the counter in-between you and RIKKA, you should still be able to pickpocket her and are free to steal items with minimal risk of being caught. Plus her eye meter doesn't go back up either. My percentage of being caught was 5% per item.
7. Steal each item one at a time until she runs out. Steal them one at a time because each theft counts as a separate pickpocket. I didn't get an exact count but it was around ten items, probably more.
8. add edit: (Credit goes to Liiami) To get the remaining required number of pickpockets just sell Rikka items and steal them back.

Good Luck and Happy Hunting!

You need to pickpocket 20 times (characters) without being caught for that pickpocket attempt. You can pickpocket from the same character multiple times. I always backed out of the pickpocket screen to make sure the pickpocket counted.

You can track how many characters pickpocketed under Status -> Stats -> Social -> Characters Pickpocketed

I found a nice little loop for pickpocketing in Gorhart. Starting in the Inn, there is a girl on the second floor eating at a table. You'll have to go in the room behind her until she's unsuspecting. Take her gold, then leave the Inn. Directly across from the Inn is a field with two citizens working it. You can pickpocket both of them and then just to the east as you head back to the Inn is a man feeding his chickens. You need to go into stealth before you even round the corner and pickpocket him as soon as you get the option. Now head back into the Inn, rinse, and repeat.

You may need to Fateweave yourself into a Finesse character with high stealth skills to do this but if you do, it'll go moderately quickly. Unfortunately, they won't have gold on them every time at the one feeding his chicken is only good for two pickpockets.

Of course, you could always attempt to pickpocket before you backstab and go two for one.