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It's an interesting one and a dilemma that's been hot on my mind for a long time now.
I've introduced game to some people and worked with PUAs etc.
Oftentimes it works really well because they have a level of inner game or competency.
Sometimes, like your friend however - they just lack that core inner game. And I just think to myself...my god...this guy requires some massive overhaul of his entire life systems before he could even start to learn game. Learning 'game' as we conventionally know it for these people is not something I would necessarily recommend. I know one guy like this who's been into this stuff for like a year now but still can't really bag results. And to me it's so clear why - he's just a deep-rooted nice, quiet & shy guy. Really clever, great job etc. But just can't break out of his beta habits.
I have one close friend who's in this situation at the moment. I started introducing him to game by taking him out with a wing of mine and myself and picking up some girls to show him what is possible. I think you need to provide both a stick and a carrot - this of course was the carrot. A stick and carrot helps provide motivation, and that is what they need.
Trying to get someone field practice who has bad inner game like this, however, is a bad idea in my opinion. They will only fail and their poor self-esteem will be reinforced by this failure.
So they need to at least understand inner game (even if they cannot attain it) before practising outer game.
After that, I would treat it psychologically as a phobia, with a mixture of two classical techniques - one is systematic desensitization, i.e. to take baby steps, such as asking strangers on the street for directions to a train station. The other technique is overload (known by many different names), where you just chuck them right in the deep end. So, making approaches with a dildo strapped to your forehead. If you can make them do the second technique (unlikely), awesome. But certainly use the first.
In summary - I would be careful. I would provide a stick and carrot, then don't try to push him anymore. His inner game is so fragile, and it requires such a massive structural overhaul of his character that it's a dangerous and difficult situation. Take him out, show him what's possible. Then if he asks questions, take it to the next step. Don't force anything on him. Such a change can only come from within.
Sir, you just took those thoughts straight out of my head. I agree 100% with Rafiel's advice, and I think he hit the nail on the head.
My best friend used to have the EXACT same problem! What brought him out of his shell, turned him into a party animal, and led him to NATURALLY getting girls left and right? He moved to a college town with me, dove right into the deep end of all the craziness up here, and suddenly leapt out of his shell! I think that if you cannot spare the time and patience to take things slowly with your roomie, I would try to insert him right into ground zero of the action. Submerging one's self in the middle of anything is usually an effective way to open up and blossom.
The only downside to it is that it works best if it's their CHOICE. Forcing somebody into it might end up taking more time.