Fun Questions to Ask

Conversation is a difficult skill, and not one that everyone can master. At first glance, this might appear to be an exaggerated point of view, blowing a simple, every-day task out of proportion. But if we take a minute to really think about it, it is clear as day. The world operates on conversations. Every single aspect of a conversation has to be handled with dexterity comparable to an illusionist handling cards. How do you start the conversation? 

What if the ice-breaker is too on-the-nose, witless, too “cringe”? What if the conversation dies down in the middle, approaching the conversational equivalent of quicksand that is awkward silence? What if you have to end the conversation early but don’t want to offend the other party? These questions present real problems and solutions to such problems exist, ironically, also in the form of questions. But what makes these questions so special? Well, it’s pretty simple, really. They’re fun.

1). Hey, is that a spoon?

Right off the bat, we have a winner. This ice-breaker is like using a ramp to launch your car into the air and landing perfectly on the track, the track being the conversation. How, you may ask? The answer is simple. The natural response to this question should be the denial of the spoon’s existence in said position, whatever it may be. Perfect way to bring up “You’re right…there is no spoon.” A Matrix reference as an ice-breaker? Conversation 101. A warning to the less experienced: please do not use this one at meals because then you will have to exile yourself from society.

2). How many seconds does it take for you to run over to *insert nearby place/object* and back?

A good one to ask someone jovial and high-spirited, encouraging to go all out to answer your question. A bonus at the end could be “I bet I could do it faster.” If you can’t, they feel better and the conversation goes well. If you do beat them, well, read on to find some more questions you can use to turn the tide because even if it’s a trivial task, losing doesn’t make anyone feel good.

3). Who was the second man to step on the moon?

This one is subtle, yet masterful. Buzz Aldrin is a household name at this point in time of the 21st Century. But allow someone to answer that question correctly (as you expected) and you will see that slight hint of smugness in their posture. “Ha! Didn’t think I knew that, did you?” Makes them feel better about themselves and in general. Like I said, conversation is a skill.

4). Which sport would you like to play drunk?

Does this one even need any explanation? The correct answer to this is: any.

5). Do you think the vision about the future from Sci-Fi movies in the 90s will ever come to pass?

Referring to the flying cars, even taller buildings and cyberpunk clothing, this question demands an opinion about one of the most common images in a person’s mind. It’s like a stock photo, stuck inside our heads. We already have self-driving cars and tall buildings, and we’re not very far off from the clothing either. Some might even say that the future is now.

6). If you could be turned into an animal for one day, which one would you pick?

Everyone loves these kinds of questions, because everyone almost always doesn’t like something about themselves. People will jump at the chance to be someone else and it’s time to capitalize on that tendency. As a bonus, you might even get to hear some funny answers. Here’s one: “A trout, because I am the kind of person that swims against the current.”

7). What do you think about the Demogorgon?

A three-headed Hydra, this one. It has the power to divert the conversation into three distinct avenues; one about Stranger Things, another about Dungeons & Dragons and the final one about the general ignorance of someone living under a rock, because let’s be real. They have to have heard of at least one of those things. Ideally, it leads to a discussion about how the Demogorgon was designed from the monster in Dungeons & Dragons, which turns into a conversation about the game itself and ultimately culminates in a Dungeons & Dragons game involving the participants of the conversation. A happy ending for all.

8). Which anime would you like to live in?

Now this one is a little dangerous and depends on who you are talking to, because not everyone watches or enjoys anime. But once those conditions are taken care of, this one is solid. Every fan has dreamt of living in at least one of the anime that they have seen and will be more than happy to share their thoughts on it. Bonus tip: stay away from people who say Attack on Titan because they might be unhinged.

9). What color do you associate with each day of the week?

A rather specific and interesting question, one that will make them think for a while. Usually, there are stories associated with such concepts, one that the other party might be willing to share. Conversational success comes in many forms and this is one of them.

10). Would you look into your own future if given the chance?

This is another one of those that could lead the conversation down various diverse avenues, ranging from time travel to world domination. The future is something that intrigues almost everyone and there is not a single person alive, whatever they themselves may claim, that doesn’t want to know their own future. People who say know are just scared; if given the chance they would still look, maybe using one eye, but still. They would look.

11). Does water have a taste or is just me?

Before the conversation police are called, hear me out. Water does have a taste, depending on the source and whatever is present in it. But it’s a fun way to draw attention to a “quirk” about yourself. Even better if the person responds in a similar vein.

12). What is your weirdest 3 AM thought?

A classic. Strange thoughts make for great conversational elements. Some might help you find meaning behind them or just…add to their weirdness. Either way, it’s a win-win situation.

13). If you had *insert stupidly large amount of money*, what would you do?

Watch them struggle with choosing between ending world hunger and buying a Lamborghini with this one. But on a more serious note, this one does have the potential to be rather fun because this allows people to exercise their imagination, which most people rarely get a chance to do.

14). If you were stuck on an island, which two books would you bring with you?

This is a really good one for people who like to read, because it keeps them engaged in the conversation as it takes a turn towards a topic that they enjoy. For those who don’t like to read, this is a good way for the one who asks the question to speak about their own interests. A conversation going both ways? Now that’s something you don’t get to see every day.

15). What would you say to your favorite fictional character if you met them right at this moment?

Always a good one to pull. Who hasn’t dreamt of asking Batman to say “I’m Batman” as a child?

16). If I say “Hello There!”, you say?

If you don’t hear the words “General Kenobi” in the next 3 seconds, it is time to say goodbye.

17). Do you think aliens exist?

Yet another one that could lead the conversation into many diverse trajectories. Be it a sci-fi enthusiast or your average Joe, everybody has an opinion about aliens. A really good one is always “What if we’re the aliens?”

18). What if we’re the aliens?

You knew this one was coming.

19). If you could choose one superpower, what would you choose?

Another classic that has kept conversations going since time immemorial. There is a large list of options to choose from and the potential to get creative. Just…be careful of the ones that pick invisibility.

20). Why did they put a light inside fridges if you’re not supposed to eat in the middle of the night?

An extremely valid question. Whatever the actual reason is, pretending to be ignorant and continuing to eat at night is the Way.

21). What was your favorite thing to do as a child?

Always fun to remember your time as a child, when you had fewer concerns and getting what you wanted was as easy as asking for it. Knowledge is our bane and children have none of it. Allowing others to recall the happier memories from their childhood is bound to make the conversation go better.

23). Sure, your name is *insert name* but what would you have named yourself, if given the chance?

There is always a time in our lives when we see a different name and wish that our name was as cool…or as easy to pronounce. Not to throw shade on the names our parents were gracious enough to give us, of course. We should be proud of our names and carry them with our heads held high. But we cannot deny the simple fact that we’ve all thought about having a different name.

24). What is one thing you would change about the world?

This one will require some hardcore thinking on most people’s part. Not everyone is bothered enough to have an opinion about the state of the world in general, so it might take them a bit to arrive at an answer. But the thing is, even subconsciously, there has to be something that they do not like about how the world is. This question can be fun because, however briefly, it lets them imagine a world without the small little thing that they do not like.

25). Would you believe you if I told you that magic is real?

Keep your face as straight as possible when asking this question. Emulate any character from every magic movie ever who tells the protagonist that they are the Chosen One. Watch initial disbelief slowly turn into creeping suspicion and then brush it off with a wave of your hand.

26). If placed in Neo’s position, would you choose the Red pill or the Blue pill?

This question comes with bonuses because it lets you explain what each pill offers; the Red being the possibility of learning a disruptive truth and the Blue representing contented ignorance. Even better if you are dressed in a sleek black, extremely fashionable overcoat and pince-nez in an ominous shade of black. Consider shaving your head.

27). If you could be another person for a day, who would you be?

Extremely versatile and a good option for jump-starting a dead conversation. This question also comes bonus follow-up questions based on what they would do as the person, once switched. Would they completely uproot their life by acting like a delinquent in front of the person’s acquaintances? Something really interesting would be if they made a large donation to a charity; this way they can feel satisfied that they did some good in the world BUT none of it came from their own pocket. Win-win. Well, win-win-lose, really.

28). Would you watch a show based on your life?

The answer is no. But it might be interesting to see how the other person perceives themself. If a laugh track is mentioned, exit using the shortest route.

29). What is your favorite type of food?

This might be the perfect question because the love of food is universal and likely one of the most discussed things among friends and acquaintances. There’s even a remote chance of liking similar food, with perhaps slight differences in preparation akin to “My mom makes it like this!” You can never go wrong with food.

30). Have you ever met a famous person?

Who doesn’t like recalling the moment when they met a celebrity? It’s also likely that you will get shown pictures. But on the offhand that any celebrity has not been met, not to worry. A quick re-phrasing of the question will bring us to “If given a choice, which celebrity would you like to meet?”

31). Cat or dog?

Without mincing words, a dangerous question, to say the least. But a fun one, nonetheless. It is always entertaining to hear the Cat Cult try to explain how cats are better and then miserably fail.

Read also: Learn How to Talk Dirty with Your Partner

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