What Is the Longest Word in the Dictionary Riddle?

Have you ever come across a question, “What is the longest word in the dictionary?” It’s a little difficult question and it’s one of my favourite riddle questions.

The Riddle

The riddle goes: What is the longest word in the dictionary?
At first you might think of long scientific Words like ‘pneumonoultramicroscopicsilicovolcanoconiosis’ come to mind. But remember, riddles are meant to be clever and tricky.

The Answer

The answer to this riddle is “smiles.” Why? Because there’s a mile (word) between the first and last letters.


If you see, the word smile is not the longest word by number of letters, but if you remove the letter ‘s’ and ‘s’ from the front and last. You will see the word “miles”. This shows how riddle’s use wordplay and double meanings to make us think in creative ways.

The Longest Words in the Dictionary

  • Pneumonoultramicroscopicsilicovolcanoconiosis
  • Hippopotomonstrosesquipedaliophobia
  • Supercalifragilisticexpialidocious


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