painfulness; trouble, care (pain); trial; affliction, infliction; blow, stroke, burden, load, curse; bitter pill, bitter draught; waters of bitterness., annoyance, grievance, nuisance, vexation, mortification, sickener; bore, bother, pother, hot water, "sea of troubles" [Hamlet], hornet's nest, plague, pest., cancer, ulcer, sting, thorn; canker (bane); scorpion (evil doer); dagger (arms); scourge (instrument of punishment); carking care, canker worm of care., mishap, misfortune (adversity); desagrement, esclandre, rub., source of irritation, source of annoyance; wound, sore subject, skeleton in the closet; thorn in the flesh, thorn in one's side; where the shoe pinches, gall and wormwood., sorry sight, heavy news, provocation; affront; "head and front of one's offending" [Othello]., infestation, molestation; malignity (malevolence).

cause pain, occasion pain, give pain, bring pain, induce pain, produce pain, create pain, inflict pain [more]; pain, hurt, wound., pinch, prick, gripe (physical pain) [more]; pierce, lancinate, cut., hurt the feelings, wound the feelings, grate upon the feelings, jar upon the feelings; wring the heart, pierce the heart, lacerate the heart, break the heart, rend the heart; make the heart bleed; tear the heart strings, rend the heart strings; draw tears from the eyes., sadden; make unhappy; plunge into sorrow, grieve, fash, afflict, distress; cut up, cut to the heart., displease, annoy, incommode, discompose, trouble, disquiet; faze, feaze, feeze (U.S.); disturb, cross, perplex, molest, tease, tire, irk, vex, mortify, wherret, worry, plague, bother, pester, bore, pother, harass, harry, badger, heckle, bait, beset, infest, persecute, importune., wring, harrow, torment, torture; bullyrag; put to the rack, put to the question; break on the wheel, rack, scarify; cruciate, crucify; convulse, agonize; barb the dart; plant a dagger in the breast, plant a thorn in one's side., irritate, provoke, sting, nettle, try the patience, pique, fret, rile, tweak the nose, chafe, gall; sting to the quick, wound to the quick, cut to the quick; aggrieve, affront, enchafe, enrage, ruffle, sour the temper; give offense (resentment)., maltreat, bite, snap at, assail; smite (punish)., sicken, disgust, revolt, nauseate, disenchant, repel, offend, shock, stink in the nostrils; go against the stomach, turn the stomach; make one sick, set the teeth on edge, go against the grain, grate on the ear; stick in one's throat, stick in one's gizzard; rankle, gnaw, corrode, horrify, appal, appall, freeze the blood; make the flesh creep, make the hair stand on end; make the blood curdle, make the blood run cold; make one shudder., haunt the memory; weigh on the heart, prey on the heart, weigh on the mind, prey on the mind, weigh on the spirits, prey on the spirits; bring one's gray hairs with sorrow to the grave; add a nail to one's coffin.

causing pain, hurting; hurtful (bad); painful; dolorific, dolorous; unpleasant; unpleasing, displeasing; disagreeable, unpalatable, bitter, distasteful; uninviting; unwelcome; undesirable, undesired; obnoxious; unacceptable, unpopular, thankless., unsatisfactory, untoward, unlucky, uncomfortable., distressing; afflicting, afflictive; joyless, cheerless, comfortless; dismal, disheartening; depressing, depressive; dreary, melancholy, grievous, piteous; woeful, rueful, mournful, deplorable, pitiable, lamentable; sad, affecting, touching, pathetic., irritating, provoking, stinging, annoying, aggravating, mortifying, galling; unaccommodating, invidious, vexatious; troublesome, tiresome, irksome, wearisome; plaguing, plaguy; awkward., importunate; teasing, pestering, bothering, harassing, worrying, tormenting, carking., intolerable, insufferable, insupportable; unbearable, unendurable; past bearing; not to be borne, not to be endured; more than flesh and blood can bear; enough to drive one mad, enough to provoke a saint, enough to make a parson swear., shocking, terrific, grim, appalling, crushing; dreadful, fearful, frightful; thrilling, tremendous, dire; heart-breaking, heart-rending, heart-wounding, heart-corroding, heart-sickening; harrowing, rending., odious, hateful, execrable, repulsive, repellent, abhorrent; horrid, horrible, horrific, horrifying; offensive., nauseous, nauseating; disgusting, sickening, revolting; nasty; loathsome, loathful; fulsome; vile (bad); hideous.

painfully; with pain; deuced.

difficulty; hardness; impracticability (impossibility); tough work, hard work, uphill work; hard task, Herculean task, Augean task; task of Sisyphus, Sisyphean labor, tough job, teaser, rasper, dead lift., dilemma, embarrassment; deadlock; perplexity (uncertainty); intricacy; entanglement; cross fire; awkwardness, delicacy, ticklish card to play, knot, Gordian knot, dignus vindice nodus, net, meshes, maze; coil (convolution); crooked path; involvement., nice point, delicate point, subtle point, knotty point; vexed question, vexata quaestio, poser; puzzle (riddle); paradox; hard nut to crack, nut to crack; bone to pick, crux, pons asinorum, where the shoe pinches., nonplus, quandary, strait, pass, pinch, pretty pass, stress, brunt; critical situation, crisis; trial, rub, emergency, exigency, scramble., scrape, hobble, slough, quagmire, hot water, hornet's nest; sea of troubles, peck of troubles; pretty kettle of fish; pickle, stew, imbroglio, mess, ado; false position., set fast, stand; deadlock, dead set., fix, horns of a dilemma, cul de sac; hitch; stumblng block (hindrance).

be difficult; run one hard, go against the grain, try one's patience, put one out; put to one's shifts, put to one's wit's end; go hard with one, try one; pose, perplex (uncertain); bother, nonplus, gravel, bring to a deadlock; be impossible; be in the way of (hinder)., meet with difficulties; labor under difficulties; get into difficulties; plunge into difficulties; struggle with difficulties; contend with difficulties; grapple with difficulties; labor under a disadvantage; be in difficulty, fish in troubled waters, buffet the waves, swim against the stream, scud under bare poles., have much ado with, have a hard time of it; come to the push, come to the pinch; bear the brunt., grope in the dark, lose one's way, weave a tangled web, walk among eggs., get into a scrape; bring a hornet's nest about one's ears; be put to one's shifts; flounder, boggle, struggle; not know which way to turn (uncertain); perdre son Latin; stick at, stick in the mud, stick fast; come to a stand, come to a deadlock; hold the wolf by the ears., render difficult; enmesh, encumber, embarrass, ravel, entangle; put a spoke in the wheel (hinder); lead a pretty dance.

difficult, not easy, hard, tough; troublesome, toilsome, irksome; operose, laborious, onerous, arduous, Herculean, formidable; sooner said than done; more easily said than done., difficult to deal with, hard to deal with; ill-conditioned, crabbed; not to be handled with kid gloves, not made with rose water., awkward, unwieldy, unmanageable; intractable, stubborn (obstinate); perverse, refractory, plaguy, trying, thorny, rugged; knotted, knotty; invious; pathless, trackless; labyrinthine (convoluted); intricate, complicated (tangled); impracticable (impossible); not feasible; desperate (hopeless)., embarrassing, perplexing (uncertain); delicate, ticklish, critical; beset with difficulties, full of difficulties, surrounded by difficulties, entangled by difficulties, encompassed with difficulties.

with difficulty, with much ado; hardly; uphill; against the stream, against the grain; a rebours; invita Minerva; in the teeth of; at a pinch, upon a pinch; at long odds.