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His wife should cheat on him. Once he smells the man-juice of a competitor, it will hopefully stoke his man-fire inside. Of course he might just flip out and kill his wife. However, he may also curl up into a ball, drink and write crappy music instead. I suggest that you sleep with his wife. This way, you can give him a kick in the nuts without ever directly confronting his wussy ass. +1 if his wife's hot.

BTW - no man has ever "manned up" just by someone talking to him or telling him what to do. It takes a serious trigger and/or a profound change in basic constitution. If he's been a man-child his whole life, then do you really getting him pissed off will achieve your goal of having him "man up"?
 
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