ADJECTIVE (4)

1. without hope because there seems to be no possibility of comfort or success;
- Example: "in an agony of hopeless grief"
- Example: "with a hopeless sigh he sat down"

2. of a person unable to do something skillfully;
- Example: "I'm hopeless at mathematics"

3. certain to fail;
- Example: "the situation is hopeless"

4. (informal to emphasize how bad it is) beyond hope of management or reform;
- Example: "she handed me a hopeless jumble of papers"
- Example: "he is a hopeless romantic"

The Collaborative International Dictionary of English v.0.48:

Hopeless \Hope"less\, a.
   1. Destitute of hope; having no expectation of good;
      despairing.
      [1913 Webster]

            I am a woman, friendless, hopeless.   --Shak.
      [1913 Webster]

   2. Giving no ground of hope; promising nothing desirable;
      desperate; as, a hopeless cause.
      [1913 Webster]

            The hopelessword of "never to return"
            Breathe I against thee, upon pain of life. --Shak.
      [1913 Webster]

   3. Unhoped for; despaired of. [Obs.] --Marston. --
      Hope"less*ly, adv. -- Hope"less*ness, n.
      [1913 Webster]

WordNet (r) 3.0 (2006):

hopeless
    adj 1: without hope because there seems to be no possibility of
           comfort or success; "in an agony of hopeless grief";
           "with a hopeless sigh he sat down" [ant: hopeful]
    2: of a person unable to do something skillfully; "I'm hopeless
       at mathematics"
    3: certain to fail; "the situation is hopeless"
    4: (informal to emphasize how bad it is) beyond hope of
       management or reform; "she handed me a hopeless jumble of
       papers"; "he is a hopeless romantic"

Moby Thesaurus II by Grady Ward, 1.0:

143 Moby Thesaurus words for "hopeless":
   Laodicean, Olympian, Pollyanna, absurd, affording no hope, aloof,
   apathetic, bad, barred, benumbed, blah, blase, bleak, bootless,
   cheerless, closed-out, comatose, comfortless, contrary to reason,
   cureless, deadly, deficient, dejected, depressed, desensitized,
   despaired of, despairing, desperate, despondent, desponding,
   detached, disconsolate, discouraged, disinterested, dismal,
   done for, downcast, dull, dying, excluded, expiring, facing death,
   fatal, forlorn, funereal, futile, given up, gloomy, glum, going,
   gone, grim, heartless, hebetudinous, hoper, immedicable,
   impossible, impracticable, in a stupor, in articulo mortis,
   in despair, in extremis, inadequate, incapable of life,
   incompetent, inconceivable, inconsolable, incorrigible, incurable,
   indifferent, inept, inferior, insoluble, insouciant, irredeemable,
   irremediable, irreparable, irretrievable, languid, lethal,
   lethargic, listless, logically impossible, lost, low, lugubrious,
   melancholy, miserable, moribund, morose, near death, nonchalant,
   nonviable, not possible, numb, numbed, oxymoronic, paradoxical,
   passive, phlegmatic, pluckless, pointless, poor, preposterous,
   prohibited, resigned, ridiculous, ruled-out, sad,
   self-contradictory, sinking, slack, slipping, slipping away,
   sluggish, soporific, sorrowful, spiritless, spunkless, stoic,
   stupefied, supine, terminal, torpid, unavailing, uncaring,
   unconcerned, uncorrectable, unfit, unhappy, unhopeful,
   unimaginable, uninterested, unqualified, unthinkable, unworkable,
   useless, vain, withdrawn, without hope, woebegone, worthless,
   wretched