Ready to challenge your brain? Below are 21 riddles that seem simple at first glance but might just have you scratching your head. Remember, the answers await you at the end – but no peeking! Grab a pen and paper, and let’s see how many you can solve!
Riddles have a way of playing tricks on our minds, leading us down one path only to surprise us with an unexpected answer. From tricky wordplay to clever math puzzles, these riddles will test your logic and creativity. Ready to uncover the answers hidden in plain sight? Let’s get started!

A closeup of a person holding a jigsaw puzzle piece | Source: Pexels
Riddle #1
A woman has seven children. If half of them are boys, how can that be possible?
Riddle #2
When can three grown men, a woman, two boys, and a dog all fit under the same umbrella and still stay completely dry?
Riddle #3
Lily is a hairdresser with an unusual preference: she would rather give two blondes a haircut than one brunette. Why does she feel this way?

A female hairdresser cutting a blonde woman’s hair | Source: Midjourney
Riddle #4
A father is currently four times as old as his son. In twenty years, the father will be only twice as old as his son. How old are the father and son now?
Riddle #5
Jack, Jill, and Jane went for a walk. Jack walked twice the distance that Jill did, and Jill walked half the distance that Jane did. Together, they walked 18 miles. How far did each person walk?