Artificial intelligent assistant

smirkily

ˈsmirkily, adv.
  [f. smirky a. + -ly2.]
  = smirkingly adv.

a 1974 R. Crossman Diaries (1975) I. 135 There they were today looking at Jennie rather smugly and smirkily. 1978 Guardian Weekly 5 Feb. 18/3 Cryptic allusions..to padlocks and fetters, which most recent biographers have smirkily interpreted as meaning that he was a masochist.

Oxford English Dictionary

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