An employee wants to bet me 500 dollars that i wont shave my head bald.

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Yes

Heck no never

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Right now i have an undercut with a chin bob.
Should i do it?

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ineedadrink · 51-55, M

If you're comfortable with the idea. But the feeling of the stubble on the pillow takes a while to get used to, was my experience with super close cropped hair.