Funny Questions That Make You Think Twice
Adults - Teens

25 Funny Questions That Make You Think Twice

Quick Navigation show

We may earn money or products from the companies mentioned in this post.

25 funny questions that make you think twice? Yes and we have 25 funny questions that will make you think twice for sure.

When someone asks a question that looks easy, you instantly try to think of the easiest answer to it. It turns out that the easiest response is rarely the correct reply to questions designed to trick you, with the real answers hidden under something you’re not paying attention to.

There are hundreds of trick questions like this and they’re all excellent options when you’re trying to play a game with friends. While they jump around to suggest wrong answers because it’s the easiest route, you go ahead to correct them with facts.

25 Funny Questions That Make You Think Twice

There’s another variation for questions that don’t require answers, meant only to make you think twice and doubt reality. If you watch a lot of videos on YouTube or TikTok, you should already know what I’m talking about.

It’s not hard to see why you may want to play a game like that. In this article, I’ll show you some funny questions that will make your friends think twice and doubt reality. Before jumping in, be ready to get wowed; let’s get started.

25 Funny Questions That Make You Think Twice

1- What word is spelled incorrectly in every dictionary?

Here’s a tricky one. Dictionaries are meant to be the ultimate book for spelling since they were designed to show you the correct way to spell words and what they mean. I bet you never thought the word “incorrectly” is always spelled incorrectly though.

2- What’s a man that doesn’t have all his fingers in one hand?

Here’s another question that requires you to pay attention to details to understand what they’re driving at. Your digits should be spread evenly across both of your hands, not all of your fingers on one hand boy.

3- If you have a bowl of five oranges and you take away three, how many do you have?

Seriously, I blame our kindergarten teachers for this. While they spent their entire lives teaching us subtraction, they didn’t care to teach us that you only have what you take, not what’s left.

4- Can a man marry his widow’s sister?

Now, let’s get rid of the technicalities and take a second look at the question in question. A widow is someone without a husband. If a man has a widow, how would he possibly want to… I think I should stop here.

5- How can a man walk in the rain without an umbrella without getting his hair wet?

When you walk in the rain, your hair should get wet unless you’re using an umbrella; that’s a basic fact of life. If you’re not using an umbrella and your hair isn’t getting wet, have you ever stopped to consider if you had hair in the first place?

6- How many months have 28 days?

We all know it’s February right? Except for all other months in the year that have at least 28 days too. When next you’re trying to think of a month that has 28 days, recall that the answer is every month of the year.

7- What’s heavier; a pound of bricks or a pound of feathers?

While this is a tricky question, there’s a good chance that you’ve seen it somewhere. If you haven’t, your brain should be telling you a pound of feathers is lighter, but you shouldn’t always trust your brain; they’re both one pound each!

8- What do you sleep on, sit on, and brush your teeth with?

The trick in this question is that you try to think of sophisticated answers when the actual answer is the simplest ones: a bed, a chair, and a toothbrush. The question never specifies that it’s a single item, but your brain set that rule by itself.

9- What can you hold without having to touch it?

I always thought touch was a prerequisite for holding anything until I started holding conversations. It’s normal if you didn’t know that at first, it took me about two years to figure it out.

10- How many animals did Moses take into his ark?

And don’t tell me the bible didn’t specify the number of animals in the ark; how many times have you read the bible. In other news, you should know Moses never built an ark, it was Noah: stop focusing on the wrong part.

11- How can you drop a raw egg on a concrete floor without cracking it?

Again, getting this question wrong is another classic result of focusing on the wrong part of the question. Why do you care so much about the egg? Thankfully, the concrete doesn’t need your help not to crack; drop it anyhow you want.

12- What can you put in a bucket to reduce its weight?

It’s not feathers since feathers have mass and will increase their weight. Have you ever thought about putting a hole in your bucket? It’s a surefire way to decrease its weight; no purchase is required.

13- What comes at the end of everything?

No, it’s not death, and I don’t get why many people answer with that either. When you take a look at the end of “everything,” you find the letter “G.” I’m sure you’re probably blaming yourself for excessive thinking right now.

14- What can fill up a room and yet take up no space?

This one should be pretty easy, making it very unlikely that someone would get it wrong. You can fill up a room with light without taking up any usable space. Even after the entire space is filled up, you can still fill it up with something else, including light.

15- What must be taken before you can get it?

This question requires some out-of-the-box thinking since it looks like one of those deceptively simple ones. Sure enough, it is, because I’m not sure how you want to get a photograph without taking it. I hope you didn’t think more than twice though.

16- If you were in a race and you passed the person in second place, what position would you be in?

This is a very tricky one, but it only requires little thinking to get it right. Your brain might instantly ask you to say the first position, which is logical, but I think I’ve proven that you shouldn’t always trust that organ. Instead, the correct answer is second, I’m sure you’ve figured it out.

17- What gets wetter when it dries?

After so many examples, you still can’t seem to focus on the real point of a question. When a towel dries you, doesn’t it get wetter? Why do you have to always presume it’s the item that’s getting dried up?

18- What was the tallest mountain on Earth before the discovery of Everest?

The fact that Mount Everest wasn’t discovered at the time doesn’t mean it’s not the tallest mountain; stop mentioning the name of random mountains, please.

19- If a deaf person has to go to court, is it still a hearing?

I don’t think it should be when they can’t even hear. Also, does the right to fair hearing apply to a deaf person or is it one of the ways to discriminate against them? I hope anyone can get me answers.

20- How do you know when you run out of invisible ink?

No, I’m not asking you to overanalyze and explain; I know most invisible inks don’t become invisible immediately. However, if we had to overanalyze every joke, this world would have been a very boring place, don’t you think?

21- Why is the alphabet in that specific order?

Here is one question that I need to know. I’m not sure how English will be any different if the alphabet started with the letter R, but somewhere someday, some guy arbitrarily decided that starting with A is the best way to organize the alphabet.

22- When the lights go out, where does it go?

When people go out, they typically tell us exactly where they’re going so we know their whereabouts. I’m not sure how lights got the freedom to simply go out without telling anyone. Where exactly do they go anyway?

23- If “look” and “see” are synonymous, why are overlook and oversee opposites?

Okay, I’m sure you understand the last few questions do not have answers, including this one. I guess the founding fathers of the English language can explain why it’s so, but there are hundreds of other irregularities that need explanations about the language.

24- Why is abbreviation such a long word, when it’s meant to make things shorter?

Ignoring overlook and oversee, how come abbreviation is such a long word when its entire purpose is to make long words and phrases shorter. I guess the word could use some abbreviation itself since it’s not short in any sense.

25- Why is it an apartment when it’s always stuck together?

While I’ve answered so many questions today, I have to give up at this point and admit that I don’t know.


Things aren’t always what they seem, and you can use that simple fact to play mind tricks on people during question games. An easy way to play mind tricks is to ask questions that require thinking twice to get.

Since it’s naturally difficult to come up with those questions on your own, I can help. This article lists funny questions that make you doubt the trustworthiness of your brain.

Other Posts You Might Like:

That’s all for Funny Questions That Make You Think Twice, I think that’s a whole lot of ideas to try out have fun and enjoy.

If you find this post helpful, don’t forget to share, follow me on Pinterest, and give your rating, this would really help me know if there’s something wrong or missing in this post.

Helpful? Hit the Share Button.

Leave a Reply