My impression of "The Game" and perusing online forums where average guys who met their goals (usually dating one or two attractive women or beyond) was that those who succeeded in becoming successful at pick-up had accumulated enough experience (approaching, being rejected, follow-up encounters, escalating, taking the lead).

Similar to the old koan about how many businesses a successful entrepreneur most fail at before they succeed, I think after hundreds of encounters - you start to gain the benefits of experience. I've met and talked to a couple of these pick up artists - and they've pretty much told me they can analyze an interaction in real-time at a meta-level and know what they can do (or more likely, what their client should be doing).

There is one downside to all of the pickup techniques - it emphasizes that there is a method to the madness (and encourages subscription-based revenue - e.g. get the latest book/podcast etc.) - while from what I've observed, successful pick up artists could basically walk up to any woman (if they wanted) and say "I like peanut butter." and go from there.