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Notes -
I suppose if he does go ahead with this (hopefully in a shortened version that is better planned) it will indeed do a lot to change what he worries about; as you say, getting twisted into knots over a silly conversation at a routine party will be less of a thing when compared with "I nearly froze to death that time and had to save myself". So that may work to reduce social awkwardness because the stakes will be, by comparison, so trivial. Not caring about "am I coming across as too needy?" may indeed help him over a lot of social barriers.
But he has to be alive to do that, and so far this trip is sounding like an elaborate form of suicide. Taking risks because there's no way to reduce all risk is one thing, taking risks because you want risks that are literally life-or-death in order to achieve some psychic transformation is quite different.
The Hock is basically a homebrew form of psychological chemotherapy. Its aim is, among other things, to kill the neuroticism before it kills the human. Of course, chemotherapy administered and brewed by random jackasses is best described as 'risky as all hell'.
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