‘A penny for your thoughts’ is a common idiomatic expression that has existed since the 1500’s, appearing in a collection of proverbs by John Heywood, from 1546. It is not a proverb, however, by any strict criteria.
Meaning of Penny for Your Thoughts
We use the expression a penny for your thoughts when we wish to know what is on another person’s mind. However, we do not use this idiom randomly just anytime we want to get an opinion, etc. Instead, it is reserved for when another person we are with is unusually quiet and withdrawn, perhaps seeming introspective or distracted.
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It means simply “what are you thinking,” and we are not actually offering any monetary compensation in exchange for another person’s thoughts.

Examples Of Use
A couple, Sam and Sara, are out for dinner in their favorite restaurant. Sara is telling Sam about what happened with her sister, but Sam seems lost in his own thoughts, hardly paying attention. He’s not quite being his jovial self, Sara doesn’t want to make a big deal out of it, so she says, “A penny for your thoughts.”
This gentle prodding knocks Sam out of his reverie and he says with an apologetic smile “Oh, I’m just distracted by this big deadline at work. No big deal.”
Origin
The word penny itself dates back many hundreds of years, coming from the Anglo-Saxon word pening or penig. The German cognate was pfennig. This was a monetary unit of currency having two denominations, the greater at one-fifth of a shilling, and the less, as one-twelfth of a shilling. Although the British pound was not divided into 100 equal parts like our American dollar, its smallest unit was called a penny, which is where we got our word for 1/100th of a dollar. At one time, the word was commonly used as a synonym for ‘coin.’ This gave rise to many expressions, such as “a pretty penny,” which would refer to a great sum of money, as opposed to an attractive penny.
Similar expressions to ‘penny for your thoughts’ have existed such as pennyworth of wit (penn’orth of wit). There are also other English expressions which use the word penny to refer to thoughts.
Song
Penny for your Thoughts is also the title of a song written in the late 1800’s by Stephen Foster, known as the ‘Father of American Music.’
Beginning Lyrics
A penny for your thoughts?
Do you think that you will love her
When all those burning dreams have flitted from your heart?
A penny for your thoughts!
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