Artful Pocketer Achievement
Pick 50 pockets.
For this achievement you must pick pocket 50 items. You can pick pocket by crouching down and then tapping when hidden from the target. To maximize results, do it at night (if outside) with a high stealth level, low / no armor, and a stealth boy active if desired.
The best place to farm this achievement is within the Vault 21 reception area. The receptionist will have the item; "Bubblegum" on her person. If you pickpocket this item from her, the item will never go away, so you can continuously steal this from her. Having a high Stealth skill, using a StealthBoy makes this achievement go by much faster.