Funny Questions To Ask – How To Become A Funny Conversationalist

Having a list of funny questions to ask people can be a game-changer for your conversational abilities. Humor is a great way to reduce tensions, lighten up a serious situation, or break the ice with a stranger or crush.  

Whether you’re trying to cheer up a co-worker, make a friend smile, or impress your crush, humor can work for you. 

Unfortunately, not everyone is naturally funny. Each person has their own sense of humor and might find different things funny than others. 

Myself, for example, I have a dark, twisted sense of humor. I often make jokes that I shouldn’t, which might offend some people. But most of my friends find it hilarious and appreciate my quick wit. 

Funny Questions To Ask

If you want to be known as a walking stand-up routine, we’ve got some funny questions to ask someone that is sure to get a hilarious response. We’ve split these into categories in case you’re in a need for something specific. Or save the list so you can use them all. I don’t mind!

Asking questions is a great way to get to know someone or just to provide some entertainment when you need a topic of conversation or a way to pass the time. 

You don’t always have to be serious and ask serious questions like “What’s your dream job?” or “What do you want to do with your future?” 

I happen to think it’s more interesting to discuss hypothetical situations and original topics that I’m not used to having to answer. It makes the conversation more interesting.

We’ve put together a list of the twenty-eight best funny questions to ask, divided into categories like silly, hypothetical, interesting, weird, and crazy would you rather’s. Let’s get started!

Get Silly With These Six Questions

Sometimes, you just want a question that’s going to make your companion laugh. You know it’s not a serious topic but that’s okay. You don’t always have to have in-depth deep convos with someone to bond. Try these six silly questions to ask the next time you think someone needs a laugh.

  1. What would be the creepiest thing to say to a stranger walking past you?
  2. Would cereal be considered soup?
  3. What body part do you wish you could detach?
  4. Is a hotdog also a sandwich?
  5. What’s the stupidest fact you know? 
  6. What two normal things become weird if you do them one after the other?

Hypothetical Possibilities

Hypothetical situations make for some interesting questions to ask people. I enjoy hearing completely different responses. It helps demonstrate what I’m always saying – we’re all unique and have our own way of thinking.

Hypotheticals can also give you valuable insight into a person’s psyche. You might suddenly realize the shy quiet person who seems completely harmless would actually be the warlord of a country if given the right parameters. 

Here are six interesting questions to ask someone about hypothetical situations. 

  1. If your browsing history was hacked, how much would you pay to keep the information from being publicly released?
  2. If you could time travel to one place, where would you go?
  3. During an apocalypse, what would your role be? Would you try to go solo or join a group?
  4. If you could have one superpower, what would you choose?
  5. If you were President, what is the first law you would change?

Interesting Queries

Each of us has a life story to tell. We’ve all experienced trials and tribulations, hardships, and heartbreaks. Sharing our experience with others is a great way to bond. 

Here are six interesting questions to ask someone to learn more about each other.

  1. What’s your biggest peeve?
  2. Do you consider yourself a leader or a follower?
  3. What is your biggest regret?
  4. Which accomplishment are you most proud to have done?
  5. What personality trait has caused you the most problems?
  6. What is your best attribute?

 Weird Situations

Sometimes, it’s nice to escape reality and imagine impossible scenarios. I love conversations where I have to use my imagination. It’s always interesting to me to compare what I would envision with everyone else. 

When you’ve had a long day and need an escape, or if you’re trying to break free of boredom, weird questions can be a great tool. Take a break from life and try these six weird questions to ask someone.

  1. If you could design a race of aliens, what would you create?
  2. What would you use to replace your hands besides hooks or clamps?
  3. If you had the power to combine two animals to make a new breed, what would you design?
  4. Would you want to be one of the first people to colonize a new planet? Where would you want to live?
  5. If you could have an unlimited supply of one thing, what would you choose?
  6. If animals could talk, which creature would be the rudest? The politest? 

Crazy Would You Rather Scenarios

Everyone has had someone ask them “would you rather” questions. Sometimes, it might be because you’re making plans. Or it could be a hypothetical situation that has very little chance of ever happening.

For me, it was a game. Decades ago, when I was an adolescent, my friends and I would play would you rather date this guy or that guy. We’d always pick celebrities and make fun of each other’s choices. 

Now, here are six crazy questions to ask when you’re at a lull in conversation or you’re just trying to lighten the mood.

  1. Would you rather have all green lights in traffic or never have to stand in line again?
  2. If you had to choose, would you live in an RV or a sailboat for the rest of your life?
  3. Which would you prefer? The ability to see your future or be able to change your past?
  4. Would you rather have to dance every time you heard music or sing? 
  5. Would you rather have skin that changes colors with your mood or tattoos that appear on your body showing what you did the day before?
  6. Teleport anywhere or read minds?

Get The Conversation Started with These Funny Questions

We’ve given you twenty-eight funny questions to ask friends, family, or romantic partners. You could even ask complete strangers! Or do as my kids, and use these funny questions to ask Alexa. These funny topics are sure to provide entertaining conversations. But, be sure you’re answering the same questions you’re asking so it’s not a one-way street. Happy chatting!