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"