Riddles of the old

Riddles have been here as long as literacy. Not online riddle games like Tailored Riddles, of course (even though it has been said that Abe Lincoln enjoyed a game or two of Tailored Riddles, I saw it on Facebook). We have dug through Wikipedia and found some really cool ancient riddles for you to have fun with.

Abe Lincoln enjoyed a game or two of Tailored Riddles


Some riddles have been found even in the old Babylon culture. However, as researchers have not been able to find answers, these are here purely as entertainment and purely for you to guess answers:

‘My knees hasten, my feet do not rest, a shepherd without pity drives me to pasture’

‘You went and took the enemy’s property; the enemy came and took your property’

‘Who becomes pregnant without conceiving, who becomes fat without eating?’

As we said, researchers were not able to find answers to these riddles, but it can definitely show that old Babylonians enjoyed a brainteaser or two. Possibly even Hammurabi used these to get some rest from practicing law.


It is thought that the oldest written records of riddles of any kind are found in the Sanskrt Rigveda. There they use a term prahelikā, which is as close to the English term “riddle” as possible. There are other explanations for the term, though, as the etymology is yet undefined. Also, in Sanskrt, riddles are mentioned in Atharvaveda and other Vedic texts.

Riddles are also present in Rigveda

An example of such riddles:

‘Who moves in the air?
Who makes a noise on seeing a thief?
Who is the enemy of lotuses?
Who is the climax of fury?’

The riddles need to be solved in Sanskrt, so you obviously have no chance. But the interesting thing is that they had a really cool concept. They asked 4 questions, however the idea is that you combine the answers to questions 1, 2 and 3 to get the final answer to 4. The first answer is bird (vi), the second dog (çva), the third sun (mitra), and the whole is Viçvamitra, Rama’s first teacher and counselor and a man noted for his outbursts of rage.

The Bible

Though not numerous, riddles are very present in the Bible as well. Probably the most famous one is the Samson’s riddle:

“Out of the eater, something to eat; out of the strong, something sweet”

Not really a fair riddle, as you cannot really deduct the answer (“What do I have in my pocket?” anyone?). Neither could the thirty Philistine guests, who the riddle was posed to by Samson. The answer is based on Samson’s personal experience, when he slew a lion and after a while found bees and honey in his corpse. The expected answer was “What is sweeter than honey? What is stronger than a lion?” In case you got this one right, I suggest we proclaim you the all time riddle champion forever.

Ancient Greece

We could not do a real overview of riddles of the old without touching upon Ancient Greece. Greeks of the time had a lot of riddles, even the oracles spoke in a riddling manor. But, probably the most famous riddle of all the Greek riddles is the one that the mighty Sphinx posed to Oedipus.

Oedipus and the Sphinx by Francois-Xavier Fabre

“Which creature has one voice and yet becomes four-footed and two-footed and three-footed?”

This one is actually quite similar to the riddles of today, so we will allow you to take a whack at it.
If you want to learn the solution that Oedipus found, please click here.

By some sources, there was a second riddle:

“There are two sisters: one gives birth to the other and she, in turn, gives birth to the first. Who are the two sisters?”

This one can also be deduced. Though note that the term “sister” is not necessarily precise in the English language, it works much better in Ancient Greek.
Click here to see who the two sisters are.

So, what about today?

Today, in a world of seven billion people, there are more and more kinds of riddles every day. Of course, with the growth of technology, some of these use tools or technical concepts. However, most of them are still open to general public so anyone can solve them.

At Tailored Riddles, we are trying a different approach to riddling – we want to make a riddle around the player. So, player A and player B will not get the same riddles, and will require different skills and experiences to solve them. Don’t believe us? Give it a go! We appreciate any feedback you might leave us.

Recent posts

Getting Started

Tailored Riddles allows you to build a riddle game about you. It is original, individual and challenges the mind ­whether as a gift to a friend or for your personal amusement.

Try Demo 3 Free Levels Build Custom Riddles Starting at $5