Etymology
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Words related to gentleman

gentle (adj.)
early 13c., gentile, gentle "well-born, of noble rank or family," from Old French gentil/jentil "high-born, worthy, noble, of good family; courageous, valiant; fine, good, fair" (11c., in Modern French "nice, graceful, pleasing; fine, pretty") and directly from Latin gentilis "of the same family or clan," in Medieval Latin "of noble or good birth," from gens (genitive gentis) "race, clan," from root of gignere "beget," from PIE root *gene- "to give birth, beget," from PIE root *gene- "give birth, beget," with derivatives referring to procreation and familial and tribal groups.

Sense evolved in English and French to "having the character or manners of one of noble rank or birth," varying according to how those were defined. From mid-13c. in English as "gracious, kind" (now obsolete), manners prescribed for Christian or chivalrous nobility. From late 13c. as "courteous, polite, well-bred, charming;" c. 1300 as "graceful, beautiful." Meaning "mild, tender; easy; not harsh" (of animals, things, persons) is from 1550s. Older sense remains in gentleman, and compare gentile (adj.), an alternative form which tends to keep the Biblical senses of the Latin word (though gentle in Middle English sometimes meant "pagan, heathen"), and genteel, which is the same word borrowed again from French. From 1823 as "pertaining to the fairies."
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man (n.)
Origin and meaning of man

"a featherless plantigrade biped mammal of the genus Homo" [Century Dictionary], Old English man, mann "human being, person (male or female); brave man, hero;" also "servant, vassal, adult male considered as under the control of another person," from Proto-Germanic *mann- (source also of Old Saxon, Swedish, Dutch, Old High German man, Old Frisian mon, German Mann, Old Norse maðr, Danish mand, Gothic manna "man"), from PIE root *man- (1) "man." For the plural, see men.

Sometimes connected to root *men- (1) "to think," which would make the ground sense of man "one who has intelligence," but not all linguists accept this. Liberman, for instance, writes, "Most probably man 'human being' is a secularized divine name" from Mannus [Tacitus, "Germania," chap. 2], "believed to be the progenitor of the human race."

Specific sense of "adult male of the human race" (distinguished from a woman or boy) is by late Old English (c. 1000); Old English used wer and wif to distinguish the sexes, but wer began to disappear late 13c. and was replaced by man. Universal sense of the word remains in mankind and manslaughter. Similarly, Latin had homo "human being" and vir "adult male human being," but they merged in Vulgar Latin, with homo extended to both senses. A like evolution took place in Slavic languages, and in some of them the word has narrowed to mean "husband." PIE had two other "man" roots: *uiHro "freeman" (source of Sanskrit vira-, Lithuanian vyras, Latin vir, Old Irish fer, Gothic wair; see *wi-ro-) and *hner "man," a title more of honor than *uiHro (source of Sanskrit nar-, Armenian ayr, Welsh ner, Greek anēr; see *ner- (2)).

Man also was in Old English as an indefinite pronoun, "one, people, they." It was used generically for "the human race, mankind" by c. 1200. As a word of familiar address, originally often implying impatience, c.1400; hence probably its use as an interjection of surprise or emphasis, since Middle English but especially popular from early 20c.

As "a woman's lover," by mid-14c. As "adult male possessing manly qualities in an eminent degree," from 14c. Man's man, one whose qualities are appreciated by other men, is by 1873. Colloquial use of the Man for "the boss" is by 1918. To be man or mouse "be brave or be timid" is from 1540s. Meaning "piece with which a game (especially chess) is played" is from c. 1400.

Man-about-town "man of the leisure class who frequents clubs, theaters, and other social resorts" is from 1734. Man of the world is from mid-14c. as "secular man, layman;" by early 15c. as "man experienced in the ways of the world, one able to take things in stride." To do something as one man "unanimously" is from late 14c.

So I am as he that seythe, 'Come hyddr John, my man.' [1473]
MANTRAP, a woman's commodity. [Grose, "Dictionary of the Vulgar Tongue," London, 1785]
At the kinges court, my brother, Ech man for himself. [Chaucer, "Knight's Tale," c. 1386]
gent (n.)
colloquial shortening of gentleman, by 17c. (in early uses it is difficult to distinguish the shortening from the common abbreviation gent.), which is perhaps the origin of this use. "Early in the nineteenth century the word was colloquial and slightly jocular; about 1840 its use came to be regarded as a mark of low breeding" [OED].
gentlemanly (adj.)
early 15c., "well-behaved, courteous," from gentleman + -ly (1).