Etymology
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misery (n.)

late 14c., "state of grievous affliction, condition of external unhappiness," from Old French misere "miserable situation, misfortune, distress" (12c.), from Latin miseria "wretchedness," from miser "wretched, pitiable" (see miser). Meaning "condition of one in great sorrow or mental distress" is from 1530s.

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plaintive (adj.)

late 14c., "lamenting, complaining, giving utterance to sorrow or grief," from Old French plaintif "complaining; wretched, miserable," from plainte (see plaint). Sense of "expressive of sorrow or melancholy, mournful, sad" is recorded from 1570s. Earlier was pleintful "grievous, lamentable" (early 14c.). Related: Plaintively; plaintiveness.

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desolate (adj.)

mid-14c., of persons, "disconsolate, miserable, overwhelmed with grief, deprived of comfort;" late 14c., of persons, "without companions, solitary, lonely;" also, of places, "uninhabited, abandoned," from Latin desolatus, past participle of desolare "leave alone, desert," from de- "completely" (see de-) + solare "make lonely," from solus "alone" (see sole (adj.)). Related: Desolately; desolateness.

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plaintiff (n.)

in law, "the person who begins a suit before a tribunal for the recovery of a claim" (opposed to defendant), c. 1400, pleintif, from Anglo-French pleintif (late 13c.), from noun use of Old French plaintif "complaining; wretched, miserable," in law, "aggrieved" (as in partie plaintif "the party bringing a suit at law"), from plainte (see plaint). Identical with plaintive at first; the form that receded into legal usage retained the older -iff spelling.

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hovel (n.)

mid-14c., "roofed passage, vent for smoke," later "shed for animals" (mid-15c.), of unknown origin. The proposal that it is a diminutive of Old English hof "dwellings, farm" is "etymologically and chronologically inadmissible" [OED]. Meaning "shed for human habitation; rude or miserable cabin" is from 1620s. It also sometimes meant "canopied niche for a statue or image" (mid-15c.).

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truant (n.)
c. 1200, "beggar, vagabond," from Old French truant "beggar, rogue" (12c.), as an adjective, "wretched, miserable, of low caste," from Gaulish *trougant- (compare Breton *truan, later truant "vagabond," Welsh truan "wretch," Gaelic truaghan "wretched"), of uncertain origin. Compare Spanish truhan "buffoon," from same source. Meaning "one who wanders from an appointed place," especially "a child who stays away from school without leave" is first attested mid-15c.
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caitiff (adj.)
c. 1300, "wicked, base, cowardly," from Old North French caitive "captive, miserable" (Old French chaitif, 12c., Modern French chétif "puny, sickly, poor, weak"), from Latin captivus "caught, taken prisoner," from captus, past participle of capere "to take, hold, seize," from PIE root *kap- "to grasp." Its doublet, captive, is a later, scholarly borrowing of the same word. In most Romance languages, it has acquired a pejorative sense (Spanish cautivo, Italian cattivo).
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malinger (v.)

"to pretend illness to escape duty," 1820, from French malingrer "to suffer," a slang word that probably also at one time meant "pretend to be ill," from malingre "ailing, sickly" (13c.), which is of uncertain origin, possibly a blend of mingre "sickly, miserable" and malade "ill." Mingre is itself a blend of maigre "meager" (see meager) + haingre "sick, haggard," which is possibly from Germanic (compare Middle High German hager "thin").

The sense evolution in French would be through the notion of beggars who feigned to be sick or exhibited sham sores to excite compassion. Malingerer is attested from 1761, in a translation of de Saxe; malingering as a verbal noun is attested from 1778. Related: Malingered.

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mesel 

"leprous" (adj.); "a leper" (n.); both c. 1300, from Old French mesel "wretched, leprous; a wretch," from Latin misellus "wretched, unfortunate," as a noun, "a wretch," in Medieval Latin, "a leper," diminutive of miser "wretched, unfortunate, miserable" (see miser). A Latin diminutive form without diminutive force. Also from Latin misellus are Old Italian misello "sick, leprous," Catalan mesell "sick." The English word is archaic or obsolete since the 1500s, replaced by leper, leprous, but its lexical DNA survives, apparently, as a contamination of measles.

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careful (adj.)

Old English cearful "mournful, sad," also "full of care or woe; anxious; full of concern" (for someone or something), thus "applying attention, painstaking, circumspect" (late Old English), the main modern sense; from care (n.) + -ful. In Middle English also "miserable, unfortunate," of persons or things; "causing fear, frightening, terrible." Careful-bed (early 14c.) was "sick-bed;" careful-day (c. 1200) was "judgment day."

Dragons dryfes doun
With kene carefull crie.
["The Wars of Alexander," c. 1400]
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