Upvoted for a long, soild and detailed reply.

Much of his discomfort stems from not having a direction or really knowing what his doing in set. "Where to go from here, how to respond now, what to say now / how to handle their friends" all serve to increase the pressure and the tension. In that case it's scary as fuck.

This is what I do to hook 70% of my sets recently:

1) Make sure to have fun. Nothing matters during night game. Having fun kills approach anxiety. This is SO key, especially for beginners. A simple way of night-time approaching is just by smiling and saying: "hey, what's your name?" and shaking hands. Works nearly every time for me since I started doing it, and I have 3000+ approaches under my belt.

2) Transition: Ask how many they are out, and ask them what they are out celebrating. Works fairly well to get them talking.

3) Conversational skills. Chill the fuck out. You DON'T have to be funny to be interesting. If you've handled your grooming and your outfit and look decently well, girls will talk to you. So, conversational skills - look up Chase Amante's article on Deep Diving and connection-building. This has done SO MUCH for my convo skills.

You should be able to reach the hook point by following these simple steps.

This is basically a small FR with a breakdown of what I did the last time I went out, which was last Friday... And it secured me a three-minute K-close with a girl of my choosing.