Artificial intelligent assistant

smirkingly

ˈsmirkingly, adv.
  [f. prec.]
  In a smirking manner; with a smirk.

1567 Drant Horace, Ep. i. vi. D ij, Thou thy selfe moste smerkinglye..Saye father, brother, to eche one. 1748 Richardson Clarissa (1811) V. 147 Hanging smirkingly upon all I said. 1773 J. Berridge Wks. (1864) 89 It would do you good to see how smirkingly they go to church in summer. 1856 W. White Through Tyrol xiii. 273 The bridegroom..looked as smirkingly jovial as could be expected.

Oxford English Dictionary

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