‘Round and Round’ Riddle

Main Piece

Phrase: “Round and round the rugged rock the ragged rascal ran. If you can tell me how many r’s are in that, you’ll be a clever man.”

Typical Answer: “7”

Actual / Trick Answer: “0”


This riddle tricks the listener into counting the number of “r’s” in the above phrase, but can literally be interpreted as asking the listener to count the number of “r’s” in the word “that.”

Personal Interpretation: This is an example of a classic variety of children’s riddles that plays with the meaning and pattern of words in order to trick the listener. It’s a “gotcha!” style riddle, as the actual question the riddle is asking isn’t immediately clear. It’s primarily meant to serve and entertain the teller of the riddle, as they know the catch and are waiting for another party (who hasn’t heard it or an oicotypical variation of it before) to walk into it.


My informant is a practicing speech pathologist in Pasadena, California. She is in her 70s and of European descent (English, Irish, and Welsh). She first recalls hearing this proverb while attending elementary school in Kansas. She remembers many schoolchildren there enjoying riddles, and using them frequently as entertainment for themselves and others.