Artificial intelligent assistant

smilesmirk

smilesmirk, v. nonce-wd.
  (ˈsmaɪlsmɜːk)
  [f. smile v. + smirk v.]
  intr. To smile in a smirking manner.

1922 Joyce Ulysses 262 She smilesmirked supercilious.

Oxford English Dictionary

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