ruffian n.

Middle English rough (late 14c.), also rouhe, rouwe, roghe, rugh, etc., from Old English ruh, rug- "not smooth to the touch, coarse (of cloth); hairy, shaggy;" of hides, "undressed, untrimmed;" of ground, "uncultivated." This is from West Germanic *rukhwaz "shaggy, hairy, rough" (source also of Middle Dutch ruuch, Dutch ruig, Old High German ruher, German rauh), from Proto-Germanic *rukhaz, which is perhaps related to the source of Sanskrit ruksah "rough;" Latin ruere "to rush, fall violently, collapse," ruina "a collapse;" Lithuanian raukas "wrinkle," rukti "to shrink."

The original -gh- sound was guttural, as in Scottish loch. The form row was a regular variant from early 16c. and lingered in dialects. Of actions, "characterized by harshness or disparity," c. 1300; of land, terrain, late 15c. as "rugged, hard to traverse." Of stormy weather from mid-14c.; by late 14c. of turbulent seas, rude language, discordant sounds.

From mid-14c. as "crudely made;" c. 1600 as "rudely sufficient, not smooth or formed by art." Rough stone "undressed stone mortared together" is from mid-15c. Of writing or literary style, "lacking refinement, unpolished," 1530s. The sense of "approximate" is recorded from c. 1600.

Rough draft (or draught) is from 1690s. Rough-and-ready "rude and disorderly" is by 1832, from an earlier noun (1810), originally military; rough-and-tumble "not elaborately or carefully ordered" is from a style of free-fighting characterized by indiscriminate blows and falls (1810). Rough music "din produced by banging pots, pans, etc. for the purpose of annoying or punishing a neighbor" is by 1708. Rough-snout (c. 1300) was an old term for "a bearded face."

1530s, "sweetheart," a term of endearment applied to either sex, of uncertain origin; perhaps from Dutch boel "lover; brother," which probably is a diminutive of Middle Dutch broeder "brother" (compare Middle High German buole "brother," source of German Buhle "lover;" see brother (n.)).

The meaning deteriorated 17c. through "fine fellow" and "blusterer" to "harasser of the weak" (1680s, from bully-ruffian, 1650s). Perhaps this was by influence of bull (n.1), but a connecting sense between "lover" and "ruffian" might be "protector of a prostitute," which was one sense of bully (though it is not specifically attested until 1706). "Sweetheart" words often go bad in this way; compare leman, also ladybird, which in Farmer and Henley ("Slang and Its Analogues") is "1. A whore; and (2) a term of endearment." Shakespeare has bully-rook "jolly comrade."

The adjective meaning "worthy, jolly, admirable" is attested from 1680s and preserves an earlier, positive sense of the word. It enjoyed popularity in late 19c. American English, and was used from 1864 in expressions, such as bully for you! "bravo!"

c. 1200, "broken ground, a rough surface," from rough (adj.). From 1640s as "the disagreeable side of anything." The meaning "a rowdy" is attested by 1837, but Century Dictionary calls this perhaps rather an abbreviation of ruffian conformed in spelling to rough. The specific sense in golf, in reference to the ground at the edge of the greens, is by 1901.

Phrase in the rough "in an unfinished or unprocessed condition" (of timber, etc.) is from 1620s, in rough diamond "diamond in its natural state," which was used figuratively, of persons, by 1700, hence diamond in the rough (by 1874 of persons, in the figurative sense "one whose good character is somewhat masked by rough manners and want of education or style").