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1. WordNet® 3.0 (2006)
disheartening
    adj 1: destructive of morale and self-reliance [syn:
           demoralizing, demoralising, disheartening,
           dispiriting]

2. The Collaborative International Dictionary of English v.0.48
Dishearten \Dis*heart"en\ (d[i^]s*h[aum]rt"'n), v. t. [imp. & p.
   p. Disheartened (d[i^]s*h[aum]rt"'nd); p. pr. & vb. n.
   Disheartening.] [Pref. dis- + hearten.]
   To discourage; to deprive of courage and hope; to depress the
   spirits of; to deject.
   [1913 Webster]

         Regiments . . . utterly disorganized and disheartened.
                                                  --Macaulay.

   Syn: To dispirit; discourage; depress; deject; deter;
        terrify.
        [1913 Webster]

3. The Collaborative International Dictionary of English v.0.48
disheartening \disheartening\ adj.
   Causing loss of hope or enthusiasm.

   Syn: demoralizing, demoralising, dispiriting.
        [WordNet 1.5 +PJC]

Thesaurus Results for disheartening:

1. Moby Thesaurus II by Grady Ward, 1.0
alarming, awing, black, bleak, chilling, daunting, depressant, depressing, depressive, despondent, deterrent, deterring, disappointing, disconcerting, discouraging, dismal, dismaying, dispiriting, displeasing, disquieting, dissatisfactory, down, dreary, fear-inspiring, fearful, fearsome, frightening, frightful, funereal, inadequate, incommensurate, insufficient, not good enough, oppressive, overawing, pessimistic, scaring, scary, somber, startling, unfulfilling, ungratifying, unsatisfactory, unsatisfying
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