Etymology
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miserable (adj.)

early 15c., "full of misery, causing wretchedness" (of conditions), from Old French miserable (14c.) and directly from Latin miserabilis "pitiable, miserable, deplorable, lamentable," from miserari "to pity, lament, deplore," from miser "wretched" (see miser). Of persons, "existing in a state of want, suffering, wretchedness, etc.," it is attested from 1520s. Meaning "mentally full of misery, wretched in feeling unhappy," by 1590s. Related: Miserableness.

The sense associated with miser, "covetous, miserly," is attested from late 15c., but by 1895 (Century Dictionary) was "obsolete or Scotch." As a noun, "an unfortunate, an unhappy creature," 1530s (reinforced later by the French cognate, as in Hugo's "Les Misérables").

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miserably (adv.)

"in a miserable manner, pitiably, deplorable," early 15c.; see miserable + -ly (2).

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miser (n.)

1540s, "miserable person, wretch," from Latin miser (adj.) "unhappy, wretched, pitiable, in distress," a word for which "no acceptable PIE pedigree has been found" [de Vaan]. The oldest English sense now is obsolete; the main modern meaning of "money-hoarding person" ("one who in wealth conducts himself as one afflicted with poverty" - Century Dictionary) is recorded by 1560s, from the presumed unhappiness of such people. The older sense is preserved in miserable, misery, etc.

Besides general wretchedness, the Latin word connoted also "intense erotic love" (compare slang got it bad "deeply infatuated") and hence was a favorite word of Catullus. In Greek a miser was kyminopristes, literally "a cumin seed splitter." In Modern Greek, he might be called hekentabelones, literally "one who has sixty needles." The German word, filz, literally "felt," preserves the image of the felt slippers which the miser often wore in caricatures. Lettish mantrausis "miser" is literally "money-raker."

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godforsaken (adj.)
also god-forsaken, God-forsaken, "forlorn, desolate, miserable," 1816, from God + forsaken.
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squalor (n.)
1620s, "state or condition of being miserable and dirty," from Latin squalor "roughness, dirtiness, filthiness," from squalere "be filthy" (see squalid).
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ratty (adj.)

1856, "resembling a rat;" 1865, "full of rats;" 1867, "wretched, miserable, shabby," from rat (n.) + -y (2). An older word for "resembling a rat" is rattish (1680s).

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pigsty (n.)

"a pig pen, a sty for pigs," 1590s, from pig (n.1) + sty (n.1). Figurative use for "miserable, dirty hovel" is attested from 1820. An older word was pighouse (late 15c.).

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caitiff (n.)
c. 1300, "wicked man, scoundrel," from Anglo-French caitif, noun use of Old North French caitive (Old French chaitif) "captive, miserable" (see caitiff (adj.)). From mid-14c as "prisoner."
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weary (adj.)
Old English werig "tired, exhausted; miserable, sad," related to worian "to wander, totter," from Proto-Germanic *worigaz (source also of Old Saxon worig "weary," Old High German wuorag "intoxicated"), of unknown origin.
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unhappy (adj.)
c. 1300, "causing misfortune or trouble (to oneself or others)," from un- (1) "not" + happy. Meaning "unfortunate, unlucky" is recorded from late 14c.; sense of "miserable, wretched" is recorded from late 14c. (originally via misfortune or mishap).
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