Synonyms for Painful:

adj.

arduous (adjective)
burdensome, grueling.
awkward (adjective)
embarrassed.
burning (adjective)
irritating.
cruel (adjective)
bitter, atrocious, poignant.
difficult (adjective)
bothersome.
distasteful (adjective)
unpalatable, offensive, abominable, odious.
doleful (adjective)
sad, dismal, woeful.
painful (adjective)
cutting, offensive, stinging, bothersome, hurtful, wrenching, stabbing, arduous, excruciating, irritating, odious, unbearable, inflaming, grievous, distressful, woeful, sore, uncomfortable, unpleasant, troublesome, crushing, horrendous, anguishing, severe, insufferable, oppressive, Besetting, miserable, annoying, aching, Gnawing, burdensome, Irksome, biting, tormenting, piercing, trying, cruel, agonizing, chafing, acute, bitter, Torturing., Cramping, aggravating, withering, throbbing, disagreeable, harrowing, smarting, grueling.
physically or mentally agonizing (adjective)
harrowing, hurtful, trying, aching, caustic, terrible, excruciating, sensitive, distressing, tender, awful, smarting, piercing, sharp, stinging, dreadful, sore, unpleasant, severe, agonizing, afflictive, disagreeable, arduous, burning, throbbing, uncomfortable, grievous, inflamed, troublesome, irritated, distasteful, biting, tormenting, extreme.
severe (adjective)
bad.
sharp (adjective)
sharp.

n.

disturbing, depressing, distasteful, heartbreaking, sad, worrying, unhappy, tragic, upsetting, dismal. guilty, awkward, humiliating, embarrassing, ignominious, shameful, pain, undignified, unfortunate, embarrassed, nagging. like, indigestible, unpalatable. painful (noun)
bitter, smarting, sensitive, agonizing, torturesome, excruciating, galled, burning, saddle sore, dreadful, abominable, racking, aching, afflictive, bad, tender, agonised, wrenching, agonized, sore, biting, Torturing., traumatic, agonising, uncomfortable, terrible, awful, torturous, unpleasant, achy, harrowing, unspeakable, poignant, chafed, atrocious, irritating.

Other synonyms:

ignominious, depressing, humiliating, nagging, shameful, upsetting, unfortunate, undignified, unhappy, heartbreaking. indigestible, embarrassed, dismal, distasteful. embarrassing, unpalatable. guilty, awkward, sad. catastrophic
tragic.
caustic
burning.
congested
inflamed.
disquieting
disturbing.
saddle-sore
saddle sore.

Usage examples for painful

  1. " I shall touch upon a painful subject, and I will tell you why. – Madeline Payne, the Detective's Daughter by Lawrence L. Lynch
  2. I have reason to know that the Duke found such an explanation a painful and trying one to make. – The Adventure of Living by John St. Loe Strachey
  3. Then I will be frank with you, George, though my being so will, as you may guess, be very painful – Can You Forgive Her? by Anthony Trollope