-Woodley is the first area in the game where you can begin pickpocketing people, animals, and even your team mates (while inside the ship). Before pickpocketing like crazy, note that each of your party members has a 2 or 3/ 10 chance of "catching" you stealing. Unfortunately, they won’t react and you’ll have no clue as to when you’ve been caught or not. Also, if they catch you in the act, you’ll automatically lose an affinity point (your relationship for your party members will be affected negatively), so pickpocket ONLY if the target has a rare or uncommon item. Most of the items that you can get can be bought or is simply trash so you shouldn’t have any problems deciding who to steal from.
-First, teach Edge the Pickpocketing manual that can be purchased from the bookstore. Buy a Bandit’s Glove and equip it to him as a wrist accessory, then approach your target and press B to attempt pickpocketing. Your chance of success depends on your current skill level for pickpocketing vs the character’s pickpocketing resistance (also with levels 1-10). You can try as many times as it takes. However, they will only carry one item at a time. A pickpocketing list will added in various locations as you go through this guide, so make use of it to help you decide your targets.