Hard Riddles With Hints and Answers

Two fathers and two sons share three cookies so everyone gets one. How is that possible?

How can you add five to nine and get two?

Forward I am heavy, but backward I am not. What am I?

What appears once in a minute, twice in a moment and never in one thousand years?

I form a ring without making a sound, and people look up when I appear. What am I?

What can reflect the past in your mind but never show you the future?

What shadow can arrive before the object that makes it?

What chair makes you stand the moment you use it?

What empty cup can fill a whole room?

What ladder goes sideways instead of up?

What pocket cannot hold money but can trap air underwater?

Two doors have two guards. One guard always lies, the other always tells the truth, and one door leads out. You may ask either guard one question. What do you ask?

Three cups sit in a row. The first two are full and the third is empty. How can you make them alternate full, empty, full by touching only one cup?

A room has no windows and no doors. Inside are a table and a mirror. How do you get out?

What is the next number: 2, 3, 5, 9, 17, ?

A station clock, a chess clock and a stopwatch all measure me, yet none can keep me once I have gone. What am I?

A gardener makes me larger by taking soil away, not by adding anything. What am I?

Shout one word into a tunnel and I return that word late, weaker, and with no idea what it means. What am I?

At midnight I may be tomorrow; by breakfast I have a new name. You can schedule me, but you can never arrive while I am still ahead. What am I?

The same photograph can make a crowd look huge or tiny, depending on which edges are cut away. What silent trick changed the truth?

The more kitchens copy me, the more meals I can make; hide me in a drawer and I feed nobody. What am I?

In a debate I may be made, missed, sharpened, or conceded, though I have no metal tip. What am I?

I arrive as a locked question with all the keys hidden in the clues. Solving me means arranging what is already there. What am I?

I may look awkward as 48 over 64, but the more you break me down by common factors, the clearer I become. What am I?