Success in pickup largely depends on how naturally one can create a chance encounter. Focusing on middle-aged women who appear friendly, approachable, and as if they haven't had sex in a while makes it surprisingly easy to get approached by them. By acting as if you're in distress—such as failing an exam, suddenly feeling dizzy, spraining an ankle, or having car trouble—you increase the likelihood of them initiating contact. Once they approach, the key is to immediately steer the interaction toward negotiation. How kind and generous will these mature, caring women be? The moment you take that first step to find out is one of the greatest thrills of pickup.