"smartphone" but with "smart" meaning "hurt" or "sting"
@Vierkantor In Spanish, "estar listo" means "to be prepared/ready", but "ser listo" means "to be smart". (Estar is for states, ser is for characteristics. Something like that.)
@varx The linguistic history of "listo" is also very interesting! "listo" meaning "smart" might have been borrowed from a form of Germanic "listiz" (art, craft; crafty), and then one of its meanings shifted via "quick" to "ready".
This is one possibility though. The counterargument against this idea is that a related word to "listo" appears in many Romance languages with the meaning "ready", and only in Spanish and Catalan it also has the meaning "clever".
@Vierkantor the first thing that "sharp" as an adjective not meaning a physical property brings to my mind is "sharp practice" and now i'm wondering how much of that sense "smart" has historically carried
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