A Penny for Your Thoughts Watch this on YouTube here - Penny Video - YouTube Video Meaning: A Penny for Your Thoughts means An invitation to a person lost in thought to share his or her preoccupation. “Penny for your thoughts?” Origin: The first known use of it is by Sir Thomas More (in 1535 it translates to say) in A Treatyce upon the last thynges, circa 1535: In such wise yt not wtoute som note & reproch of suche vagaraunte mind, other folk sodainly say to them: a peny for your thought. (A rough paraphrase of the above is "when people notice that someone appears disengaged and wish them to rejoin the conversation they ask 'a penny for your thoughts'.") This phrase was so well used that it was often shortened to 'a penny for them' or even just 'penny'. Example: Today we still hear the phrase, we say it to someone who is daydreaming, staring off at nothing, who seem preoccupied in their own thoughts. We say a penny for your thoughts to...