“Riddle me this” is the phrase I hear in my head right before someone says something deceptively simple and ruins my afternoon. This collection leans into that classic setup with questions that are short, fair, and worth trying before you scroll to the answer.
How I Use a Riddle-Me-This Round
Ask one question at a time and give people enough silence to think. I usually allow one hint, but only after everyone has made at least one real guess.
For groups, start with concrete objects before moving into wordplay and logic. That keeps the first five minutes fun instead of turning the room into twenty people silently resenting a teapot.
Classic Riddle Me This Questions
- Riddle me this: What has a face and two hands but no arms or legs?
Answer: A clock. - Riddle me this: What has a neck but no head?
Answer: A bottle. - Riddle me this: What has teeth but cannot bite?
Answer: A comb. - Riddle me this: What has one eye but cannot see?
Answer: A needle. - Riddle me this: What has many keys but opens no locks?
Answer: A piano. - Riddle me this: What has a bed but never sleeps?
Answer: A river. - Riddle me this: What has a mouth but never speaks?
Answer: A river. - Riddle me this: What has an eye at the center but never blinks?
Answer: A hurricane. - Riddle me this: What has branches but no leaves?
Answer: A bank. - Riddle me this: What has a head and tail but no body?
Answer: A coin. - Riddle me this: What gets wetter while drying?
Answer: A towel. - Riddle me this: What has a spine but no bones?
Answer: A book. - Riddle me this: What has a tongue but cannot taste?
Answer: A shoe. - Riddle me this: What can fill a room but take up no chair?
Answer: Light. - Riddle me this: What follows you in sunlight but disappears in darkness?
Answer: A shadow.
Riddle Me This Wordplay
- Riddle me this: What gets shorter when two letters are added?
Answer: Short. - Riddle me this: What begins with E, ends with E, and may contain one letter?
Answer: An envelope. - Riddle me this: What is at the end of a rainbow?
Answer: The letter W. - Riddle me this: What is in the middle of nowhere?
Answer: The letter H. - Riddle me this: What has four letters, sometimes nine, and never five?
Answer: The statement is literally counting the letters in those words. - Riddle me this: What word sounds the same after four of its five letters disappear?
Answer: Queue. - Riddle me this: What can be cracked, told, made, and played?
Answer: A joke. - Riddle me this: What belongs to you but other people use more?
Answer: Your name. - Riddle me this: What can you give and still keep?
Answer: Your word. - Riddle me this: What word becomes “one” when its first two letters vanish?
Answer: Stone. - Riddle me this: What kind of room has no doors or windows?
Answer: A mushroom. - Riddle me this: What kind of bank has no money?
Answer: A riverbank. - Riddle me this: What kind of band never plays music?
Answer: A rubber band. - Riddle me this: What kind of coat is put on wet?
Answer: A coat of paint. - Riddle me this: What is so fragile that speaking its name breaks it?
Answer: Silence.
Riddle Me This Logic and Number Questions
- Riddle me this: A farmer has 15 sheep and all but six run away. How many remain?
Answer: Six. - Riddle me this: You have two coins totaling 30 cents and one is not a nickel. What are they?
Answer: A quarter and a nickel. - Riddle me this: How many months have at least 28 days?
Answer: All 12. - Riddle me this: If you take four apples from six apples, how many do you have?
Answer: Four. - Riddle me this: How many times can you subtract 10 from 100?
Answer: Once. - Riddle me this: A clock strikes five times in four seconds. How many seconds for ten strikes?
Answer: Nine seconds. - Riddle me this: Which weighs more, 16 ounces of feathers or 16 ounces of metal?
Answer: Neither. - Riddle me this: A dozen eggs are split evenly among three people. How many does each get?
Answer: Four. - Riddle me this: What three positive whole numbers have the same sum and product?
Answer: 1, 2, and 3. - Riddle me this: A two-digit number has digits that add to 7, and the tens digit is one more than the ones digit. What is it?
Answer: 43. - Riddle me this: What two numbers add to 10 and multiply to 21?
Answer: 3 and 7. - Riddle me this: A dozen cookies are shared by four people. How many each?
Answer: Three. - Riddle me this: What is 25% of 80?
Answer: 20. - Riddle me this: A number doubled and increased by 5 equals 21. What is it?
Answer: 8. - Riddle me this: Eight people each shake hands once with every other person. How many handshakes?
Answer: 28.
Harder Riddle Me This Challenges
- Riddle me this: A woman reads a book in a dark room with no lamp or screen. How?
Answer: She is reading Braille. - Riddle me this: A child throws a ball and it comes back without touching a wall or another person. How?
Answer: The ball was thrown straight upward. - Riddle me this: A man walks through rain without an umbrella and not one hair gets wet. How?
Answer: He is bald. - Riddle me this: A woman has two children born at the same minute on the same day, but they are not twins. How?
Answer: They are part of triplets or another multiple birth. - Riddle me this: A man leaves home, turns left three times, and returns to find two masked people. Where is he?
Answer: On a baseball field. - Riddle me this: A person falls from a 20-foot ladder and walks away unharmed. How?
Answer: The person fell from a low rung. - Riddle me this: A driver goes the wrong direction on a one-way street while a police officer watches. Why is there no ticket?
Answer: The person is walking. - Riddle me this: A woman asks a restaurant server for water. The server startles her, and she says thank you. Why?
Answer: She had hiccups, and the surprise stopped them. - Riddle me this: A dog crosses a river without a bridge, boat, or getting wet. How?
Answer: The river is frozen. - Riddle me this: What grows when you remove more from it?
Answer: A hole. - Riddle me this: A woman has four daughters, and every daughter has the same brother. How many children?
Answer: Five. - Riddle me this: A person is born in room 1980 and dies in room 2050 at age 90. How?
Answer: The numbers are room numbers, not years. - Riddle me this: A man goes ten days without sleeping. How?
Answer: He sleeps at night. - Riddle me this: A plane crashes on a border. Where are the survivors buried?
Answer: Nowhere. - Riddle me this: What is always coming but changes its name when it arrives?
Answer: The future becomes the present.
Riddle Me This Speed Round
- Riddle me this: What has ears but cannot hear?
Answer: Corn. - Riddle me this: What has four wheels and flies?
Answer: A garbage truck. The flies are insects. - Riddle me this: What can run but never walks?
Answer: Water or a river. - Riddle me this: What goes up when rain comes down?
Answer: An umbrella. - Riddle me this: What can be caught but not thrown?
Answer: A cold. - Riddle me this: What has a crown but rules no country?
Answer: A pineapple. - Riddle me this: What has a bark but cannot bite?
Answer: A tree. - Riddle me this: What can travel without moving from its corner?
Answer: A postage stamp. - Riddle me this: What has holes but still holds water?
Answer: A sponge. - Riddle me this: What is yours today but will be called yesterday tomorrow?
Answer: Today.
How to Run a Riddle-Me-This Game
For a party, I use ten easy questions, ten wordplay questions, and five hard ones. That is long enough to feel like a game but short enough that people still like me afterward.
Give one point for the answer and one bonus point for explaining the trick. That rewards careful reading instead of only fast guessing.
For kids, offer category hints such as object, animal, word, or number. For adults, I wait longer before helping because watching someone overthink “a towel” is part of the experience.
The phrase “riddle me this” makes even a normal question sound like a tiny challenge, which is probably why it has lasted so long. I use it sparingly, though; after seventy questions I start sounding like a very low-budget supervillain.
As owner of Fun Riddles, Ellie curates and tests the web’s most accessible riddles, brain teasers, and lateral-thinking puzzles, organized by difficulty with hints and answers educators can trust.