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Man
Just use an opener that gives them the opportunity to talk and then let the conversation flow or notice something about them or use the best friend test ...
The possibilities are endless..
for more info notice how stand up comedians go from a subject to another and watch mystery's video about multiple-thread theory
yea, but the point is it sometimes takes ppl a little longer to discover that natural part of their game. the reason why canned openers are good is to help people get past the early stages including AA. which it sounds like where he's at. the natural fluff comes with when someone becomes comfortable with themselves.
so use the routines, and tricks as u please. eventually, u'll be comfortable enough to think on ur feet for most of the convo, and a few routines when its appropriate in the conversation. thats when it gets fun.