Testing one's abilities or requiring great effort and skill to accomplish. Can also mean questioning or disputing something.
From Old French 'chalengier' meaning 'to accuse, claim', from Latin 'calumniari' meaning 'to accuse falsely'. The sense of difficulty or demanding effort developed from the idea of confronting obstacles.
The word originally had legal connotations - challenging a jury member or challenging someone to a duel were formal legal procedures. Today's positive connotation of 'challenging' as stimulating or rewarding difficulty is relatively recent, from the mid-20th century.
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