Etymology
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guess (v.)

c. 1300, gessen "to infer from observation, perceive, find out; form an opinion, judge, decide, discern; evaluate, estimate the number, importance, etc. of," perhaps from Scandinavian (compare Middle Danish gitse, getze "to guess," Old Norse geta "guess, get"), or from or influenced by Middle Dutch gessen, Middle Low German gissen "to guess," all from Proto-Germanic *getan "to get" (see get (v.)).

The prehistoric sense evolution then would be from "get," to "take aim at," to "to estimate." Meaning "to hit upon the right answer" is from 1540s. Spelling with gu- is late 16c., sometimes attributed to Caxton and his early experience as a printer in Bruges. Related: Guessed; guessing. Guessing game attested from 1650s. To keep (someone) guessing "keep him in a state of suspense" is from 1896, American English.

[T]he legitimate, English sense of this word is to conjecture; but with us, and especially in New England, it is constantly used in common conversation instead of to believe, to suppose, to think, to imagine, to fancy. [Bartlett, "Dictionary of Americanisms," 1848]

guess (n.)

c. 1300, "indiscriminate conclusion, guesswork, doubtful supposition," from guess (v.). Mid-15c. as "considered opinion." Verbal shrug phrase your guess is as good as mine attested from 1902.

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Definitions of guess
1
guess (v.)
expect, believe, or suppose;
I guess she is angry at me for standing her up
Synonyms: think / opine / suppose / imagine / reckon
guess (v.)
put forward, of a guess, in spite of possible refutation;
I am guessing that the price of real estate will rise again
Synonyms: venture / pretend / hazard
guess (v.)
judge tentatively or form an estimate of (quantities or time);
Synonyms: estimate / gauge / approximate / judge
guess (v.)
guess correctly; solve by guessing;
He guessed the right number of beans in the jar and won the prize
Synonyms: infer
2
guess (n.)
a message expressing an opinion based on incomplete evidence;
Synonyms: conjecture / supposition / surmise / surmisal / speculation / hypothesis
guess (n.)
an estimate based on little or no information;
Synonyms: guesswork / guessing / shot / dead reckoning
From wordnet.princeton.edu