Etymology
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occupy (v.)

mid-14c., occupien, "to take possession of and retain or keep," also "to take up space or room or time; employ (someone)," irregularly borrowed from Old French ocuper, occuper "occupy (a person or place), hold, seize" (13c.) or directly from Latin occupare "take over, seize, take into possession, possess, occupy," from ob "over" (see ob-) + intensive form of capere "to grasp, seize," from PIE root *kap- "to grasp."

The final syllable of the English word is difficult to explain, but it is as old as the record; perhaps it is from a modification made in Anglo-French. During 16c.-17c. the word was a common euphemism for "have sexual intercourse with" (a sense attested from early 15c.), which caused it to fall from polite usage.

"A captaine? Gods light these villaines wil make the word as odious as the word occupy, which was an excellent good worde before it was il sorted." [Doll Tearsheet in "2 Henry IV"]

During the same time occupant could mean "prostitute." Related: Occupied; occupying.

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Definitions of occupy

occupy (v.)
keep busy with;
Synonyms: busy
occupy (v.)
live (in a certain place);
Synonyms: reside / lodge in
occupy (v.)
occupy the whole of;
Synonyms: fill
occupy (v.)
be on the mind of;
Synonyms: concern / interest / worry
occupy (v.)
march aggressively into another's territory by military force for the purposes of conquest and occupation;
Synonyms: invade
occupy (v.)
require (time or space);
This event occupied a very short time
Synonyms: take / use up
occupy (v.)
consume all of one's attention or time;
Synonyms: absorb / engross / engage
occupy (v.)
assume, as of positions or roles;
the young prince will soon occupy the throne
Synonyms: fill / take
From wordnet.princeton.edu