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It depends on the woman. Like others have said, a lot of women find bald men in hollywood attractive, but in real life they never considered dating a guy that actually shaves their head. It's so mainstream now that it's not really that different anymore.

I shave with mach 3 turbo in the shower. No mirror needed. Only have cut myself once. Are you planning on shaving it, or using clippers and cutting it without a guard? I would never Nair my head, that sounds terrible. Just throw some shaving cream and shave with the direction the hair...