One of the rare areas of social conduct with no established rules whatsoever. Pretty tricky.
I think your buddy should move all his money into Swiss bank accounts, then tell his girlfriend that he gave all of his money to charity. That way, if she goes berserk instead of commending him for his humanitarianism, he'll know she was just after his money, or just isn't a giving person. And if she's okay with it, he'll know he's got a keeper. At that point, he can ask her to sign the prenup (he's apparently got nothing to lose anyway, so she'll sign it without a second thought) or he can forget about the prenup (since she's obviously a nice person with no designs on his money anyway).
Alternatively, before he pops the question, he should just tie the engagement ring to a miniature roll of parchment with the prenup printed on it. This will show how serious he is about getting married, and will also play higher level organizational skills.
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