Artificial intelligent assistant

smirkly

ˈsmirkly, adv. Obs.—1
  [f. smirk a. + -ly2.]
  Smirkingly.

a 1586 Sidney Arcadia ii. (1622) 258 Venus was glad to heare Such proffer made, which she well shewed with smiling cheare... And smirkly thus gan say [etc.].

Oxford English Dictionary

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