Artificial intelligent assistant

dolefulness

ˈdolefulness
  [f. doleful a.1 + -ness.]
  The quality or state of being doleful; grief, sadness, sorrowfulness; dreariness, melancholy.

c 1450 Cov. Myst. (1841) 227 Ther had nevyr woman more doolfulness. 1530 Palsgr. 214/2 Dolefulnesse, tristesse. 1586 W. Webbe Eng. Poetrie (Arb.) 65 Wordes..expressing wonderfully the dolefulnesse of the song. 1887 M. E. Braddon Like & Unlike i, Sir Adrian offered no reason for dolefulness.

Oxford English Dictionary

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