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From The Collaborative International Dictionary of English v.0.44 [gcide]:
Painful \Pain"ful\, adjective
1. Full of pain; causing uneasiness or distress, either physical or mental; afflictive; disquieting; distressing. --Addison.
2. Requiring labor or toil; difficult; executed with laborious effort; as a painful service; a painful march.
3. Painstaking; careful; industrious. [Obs.] --Fuller.
A very painful person, and a great clerk. --Jer. Taylor.
Nor must the painful husbandman be tired. --Dryden.
Syn: Disquieting; troublesome; afflictive; distressing; grievous; laborious; toilsome; difficult; arduous. -- {Pain"ful*ly}, adverb -- {Pain"ful*ness}, noun
From WordNet (r) 2.0 [wn]:
painful
adjective
1: causing physical or psychological pain; "worked with painful slowness" [ant: {painless}]
2: causing misery or pain or distress; "it was a sore trial to him"; "the painful process of growing up" [syn: {afflictive}, {sore}]
3: exceptionally bad or displeasing; "atrocious taste"; "abominable workmanship"; "an awful voice"; "dreadful manners"; "a painful performance"; "terrible handwriting"; "an unspeakable odor came sweeping into the room" [syn: {atrocious}, {abominable}, {awful}, {dreadful}, {terrible}, {unspeakable}]
4: causing physical discomfort; "bites of black flies are more than irritating; they can be very painful" [syn: {irritating}]
From Moby Thesaurus II by Grady Ward, 1.0 [moby-thes]:
140 Moby Thesaurus words for "painful": Herculean, aching, achy, acute, affecting, afflictive, aggravating, agonizing, algetic, annoying, arduous, assiduous, atrocious, backbreaking, besetting, biting, bitter, bleak, bothersome, burdensome, burning, careful, cheerless, comfortless, conscientious, cramping, cruel, crushing, demanding, deplorable, depressing, depressive, detailed, diligent, discomforting, dismal, dismaying, disquieting, distasteful, distressful, distressing, disturbing, dolorific, dolorogenic, dolorous, dreary, earnest, effortful, exacting, exasperating, excruciating, forced, galling, gnawing, grave, grievous, griping, grueling, harassing, hard, hard-earned, hard-fought, harrowing, harsh, heavy, hefty, hurtful, hurting, irksome, irritating, joyless, killing, labored, laborious, lamentable, meticulous, mournful, moving, onerous, operose, oppressive, painstaking, paroxysmal, pathetic, piercing, piteous, pitiable, plaguey, poignant, pungent, punishing, racking, raw, regrettable, rigorous, rueful, sad, saddening, scrupulous, sedulous, sensitive, severe, sharp, shooting, smarting, sore, sorrowful, spasmatic, spasmic, spasmodic, stabbing, stinging, strained, strenuous, tender, thorough, thoroughgoing, throbbing, toilsome, tormenting, torturous, touching, tough, troublesome, troubling, trying, unappetizing, uncomfortable, unpalatable, unpleasant, unsavory, uphill, vexatious, vexing, wearisome, woebegone, woeful, worrisome, worrying, wretched
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