1. Noun. Any particularily puzzling event or object which prompts a puzzled scratch of the head.

2. Head scratch. Verb. Most common reaction when one spots a set of man boobs - especially when the man who is sporting the boobs is not exactly large or fat, and the occurance of the man boobs is puzzlesome, prompting the observer to scratch their head in curiosity

(Jeny scratches her head, looking puzzled)
"Jeny, why are you scratching your head?" asks Michelle.

"Well, look." (points toward a young man.) "He has man boobs... but he isnt fat." Jeny replies.

"Hmmm," ponders Michelle. "Thats a real Head Scratcher."
by mac n fode August 10, 2006
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Used to define your one friend who never gets any puss even though he's not a loser.
Why can't Jake get any action? He's a pretty nice dude and seems to do everything right but the guy can't get laid for shit. It's a real head scratcher...
by Mr.nj April 16, 2017
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