Etymology
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boob (n.)

"stupid person," 1909, American English slang, perhaps a shortening of booby. For the "woman's breast" sense, see boobs. Mencken seems to have coined booboisie (1922).

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Definitions of boob
1
boob (n.)
an ignorant or foolish person;
Synonyms: dumbbell / dummy / dope / booby / pinhead
boob (n.)
either of two soft fleshy milk-secreting glandular organs on the chest of a woman;
Synonyms: breast / bosom / knocker / tit / titty
2
boob (v.)
commit a faux pas or a fault or make a serious mistake;
Synonyms: drop the ball / sin / blunder / goof
From wordnet.princeton.edu