9 Brain Teasers and Riddles to Challenge your Friends and Family

Brain teaser cartoon head with question marks inside and confusion As brain teasers often require you to stretch your brain in unconventional ways and think outside the box, they are a great way to test your mental sharpness, keep your memory strong, reduce stress with mindful play and, of course, have a ton of fun along the way.

Here are 9 brain teasers, logic problems and riddles with answers to challenge your friends and family with. This collection of tricky riddles features a variety of brain teasers of varying difficulties. There are easy riddles for kids and more complicated brain teasers for adults.

We’ve included the solutions to each riddle. But try to challenge yourself first. How many of these puzzles and riddles can you solve without cheating?

1. The River Crossing Puzzle (Wolf, Goat and Cabbage Problem)

A farmer is heading home with a wolf, a goat and a cabbage that he purchased at the local market. He comes to a river crossing and has to rent a boat to get across. The problem is, this boat is only big enough to hold himself and a single purchase. If left unattended: The goat would eat the cabbage or the wolf would eat the goat. The farmer must be in the boat to guide it across.

So, how does the farmer get all three items and himself safely across the river?


This famous riddle has been around for centuries and requires both creative thinking and task scheduling. Both of those cognitive skills allow you to recognize that the farmer can bring things back on his return trip after he crosses the river. While it’s (purposely) not stated in the story, it’s also not expressly forbidden. Once this is known, the riddle becomes easy to solve for children and adults alike.

The farmer starts by taking the goat across before returning to grab the cabbage. Once the cabbage is brought to the other side, he’ll take the goat back with him to ensure the goat does not eat the cabbage. He will leave the goat back on the original side of the river while he takes the wolf across. Since the wolf can be safely left with the cabbage, he can then easily go back one more time to grab the goat, bring it to the other side, and get home with all three intact.

2. The Mystery Cruise

While riding along in a river, you approach a boat. This boat has not sunk. But, when you look closely, you see that there is not a single person on the boat. How is this possible?


Everyone on the boat is married.

Like many tricky riddles, this brain teaser was designed to encourage the logical part of your brain to jump forward. Our brain doesn’t like information gaps, so it likes to find the most logical answer or solution before examining all the data. This is why many people will almost immediately say “they went below deck” or “jumped overboard”.

However, like most word puzzles, you must pay attention to every detail. By focusing on the word “single”, and analyzing its other meanings, you’ll be able to crack on the code on this hard riddle.

3. Racing for the Kingdom

Realizing his reign was nearing its end, an ageing king was struggling to decide which of his two twin sons to give his kingdom too. So, he proposed they compete in a horse race to decide who would be the next king—with a rather peculiar stipulation: “Whoever’s horse crosses the finish line LAST will get the kingdom.”_

As you’d expect, both sons started the race extremely slow before finally coming across a man on the side of the road. As the man slowly walked alongside them, they explained what they were doing. He then leaned in and offered two words of advice. After that, both sons took off as fast as they could toward the finish line. What were those two words of advice?


Switch horses. The king specified that whoever’s HORSE crosses the finish line last would be the winner. So, by switching horses, each son guaranteed that winning the race on the OTHER’S horse would mean that THEIR horse will actually cross the finish line last.

Did this brain teaser stump you? By using a story format with a ton of irrelevant details thrown in, it has been designed to cause your brain to overlook the one key detail that makes this riddle easy to solve.

4. The Three Children

Johnny’s mother had three children. The first child was named "April." The second child was named "May." What was the third child’s name?



Be honest, while the solution to this riddle is obvious once you carefully read it, did you initially think the answer was “June”? That’s because our brain likes to simplify the complex work it is constantly doing by finding patterns and connections. While this is truly amazing in most scenarios, as you can see, sometimes it can also fail us.

5. Heaven or Hell Problem

You are standing in front of two large doors guarded by large soldiers. One door leads you on a path to heaven, while the other leads you to eternal damnation in hell. You’re allowed to ask one guard, one question (and one question only). You know that one solider always tells the truth and the other always lies, but you aren’t sure which one is which.


“If I ask the other guard about which side leads to heaven, what would they answer?”

Made famous in the blockbuster movie Labyrinth, this head-scratching logic puzzle has been used to challenge friends and family for centuries. It uses a trick question to answer a trick question, making it quite a favorite among puzzle lovers.

Let’s assume the left door is the one that leads to heaven.

If you asked the “truth-teller” directly which door leads to heaven, they would say “left” and, conversely, the liar would say “right”. Since you don’t know who is telling the truth or who is lying, the extra caveat in your question becomes important.

If you ask the “truth-teller”, they will tell you the honest truth about what the “liar” would say. In this case, “right”. Conversely, if you ask the “liar”, they would lie about what the “truth-teller” would say. So instead of saying “left”, the “liar” would also say “right” in this situation. So, no matter who you ask, you’ll always know which door leads to hell (or any other precarious situation) and can go through the opposite door to safety.

6. Gone with the Wind

You measure my life in hours and I serve you by expiring. I’m quick when I'm thin and slow when I'm fat. The wind is my enemy.


A candle.

This fun riddle requires you to stretch your brain and really analyze how every detail works together to create an unexpected solution. The biggest hint is the final sentence at the end about the wind.

7. The Light Switch Riddle (One Light and Three Switches)

You’re standing outside a closed room with a lightbulb inside it. The door is closed. It goes down to the floor and has no windows, so you aren’t able to see inside or know when the light is on or off. However, you are told that the light is off to start.

In front of you are three light switches, one of them controls the light. You need to determine which one that is. You can flip the switches however you want. But, you can only open the door once. And, once you do, you can no longer touch the switches. How do you figure out which switch controls the light bulb?


This is a popular riddle for kids and adults. While it doesn’t use any complex logical theory or mathematics, it does require you to expand your creative thinking. You should flip switch #1 and leave it on for a few minutes. Then switch it back to its starting point, quickly flip #2 on and then immediately open the door and walk in.

If the light is on, you know that switch #2 controls it. If the light is off, go feel it. If the bulb is hot or warm, then you know switch #1 controls it. However, if the light is not on and is cool to the touch, then the only other option is that switch #3 controls it.

8. Birthday Baffler

Alexis was born on December 31st but always celebrates her birthday in the summer. Why?


She lives in the Southern Hemisphere.

If you live in Australia, Brazil, or anywhere else south of the equator, you probably found yourself very confused as to how this is even a riddle. However, it can be quite tricky for those in the Northern Hemisphere that always associate December with winter. The fact New Year’s Eve was chosen as her birthday also causes our brains to overthink and try to create an obscure connection or pattern that doesn’t exist.

The answer to this riddle is so easy, it’s actually hard. This is kind of like when you answer “C” multiple times in a row in a test and, despite the fact you know the answer is “C” for a question, you overthink it and change the answer.

9. Age is Just a Number

A person turns 15 years old in 1990. In 1995, that same person is 10 years old. How is this possible?


We’re going prehistoric with this one! This head-scratcher is actually easier than you might think. This person was born in 2005 B.C.

So, unlike A.D. years which proceed up from year 0, B.C. years progress backwards toward year 0. So, 1995 B.C. is actually 5 years EARLIER than 1990 B.C.

So, how many of these brain teasers did you get right?

In the end, it really doesn’t matter. These riddles weren’t designed to be an IQ test, make you look like a genius or mind-reader. Instead, these types of brain teasers and riddles are a fun way to stretch your brain beyond its normal way of thinking. Which is just one of the many reasons you should exercise your brain.

Now it’s time to share these brain teasers and riddles with your friends and family and put them to the test!

Browse all puzzles