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75 Weird Questions to Ask to Start a Fun Conversation

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When you first meet someone or when you get together, the first few moments can be a little awkward, especially as a teen or tween. Why not break through that awkwardness with the perfect question or ice breaker. These 75 weird questions to ask are the secret to opening up, having fun, and getting to know other people! This can lead to great friendships, great conversations, and really getting to know someone else.

Why Ask Weird Questions?

Why Ask Weird Questions?

You might be scratching your head when it comes to why asking weird questions is a good idea, but I promise you it is a great idea! Pairing these with How Well Do You Know Me Questions is the winning combination to getting to a deeper level. These types of questions go beyond what classes you are taking and what hobbies do you have. It makes you think and really understand someone more!

Use this list of 75 weird questions to ask to help bring your relationships with others to the next level. The one thing you want to remember when using this list is that any question you ask might just be directed back at you, so be sure you are prepared to answer it too before asking it! Let’s get started!

We have divided our list into three sections:

  • Weird Questions to Ask
  • Weird Questions to Ask a Girl
  • Weird Questions to Ask a Guy

Weird Questions to Ask

Weird Questions to Ask
  • If you found a dead body lying in the neighborhood, what do you do?
  • Hopefully, they were not involved in how the body got there… You might not want to joke about that one, LOL.
  • Why is it called beauty sleep when most of us wake up looking like a train ran us over?
  • I mean, you can’t make this stuff up, right?
  • What is the most embarrassing thing you have worn this year?
  • Remember that one time when you had to borrow your brother’s sweater or your mom dressed you for family pictures.
  • Who is the 7th person on your missed called list?
  • Was it a spam call or someone you really didn’t want to talk to?
  • What color are the pants you have on right now?
  • Pants’ colors say a lot about who you are.
  • What type of light do you prefer? Warm, dright, or daylight?
  • If you didn’t realize it, lighting makes a huge difference; this is important stuff right here.
  • What is something you say all the time?
  • Mama always used to say, “life is like a box of chocolates; you never know what you are going to get!”
  • You are given a million dollars, and you have to spend it in an hour, and you can’t buy a house. What do you buy?
  • Spend it or lose it. Is it even possible to spend that so quickly?
  • Who is someone that you would really like to punch in the face?
  • We all have at least one person on this list.
  • What are the top 5 things you take in your tornado shelter with you?
  • You could be in there a long time.
  • How would you dispose of a dead body?
  • Again, don’t ask questions, just don’t.
  • What is something that you are constantly forgetting?
  • I would forget my head if it wasn’t screwed on.
  • How many times a day do you look at your phone?
  • More than I can count….
  • How many texts do you get in a day?
  • Well, let’s see can I count that high?
  • What is your best quality in a friendship?
  • Loyalty, trust, compassion…
  • What day does the week really start on, Sunday or Monday?
  • Does anyone really know the answer to this?
  • What is one superpower you do not want?
  • Hey, I probably don’t want an expert hearing; there are some things I just don’t want to hear.
  • What is something that is not important to other people but super important to you?
  • Hey, MarioKart is pretty awesome!
  • Would you really want a clone of yourself?
  • I think one is enough, right?!
  • What is your go-to drink of choice?
  • We need to know these things.
  • What is your favorite holiday?
  • Did you know National Donut Day is an actual thing?
  • Where do you see yourself in 3 hours?
  • Nothing like thinking ahead.
  • What is one thing you wish you could change the color of?
  • Hey, there are some really beautiful things that just need a new color.
  • What is the worst ice cream flavor that ever existed?
  • There are some really gross flavors out there and some that sound really gross that are actually pretty awesome.
  • What is something you hate but you have never actually tried?
  • Have you let other people’s opinions sway you that much?

Weird Questions to Ask a Girl

Weird Questions to Ask A Girl
  • Which Hogwarts teacher do you have a crush on if you had to pick one?
  • Come one, they all look pretty cute!
  • Who is the last person that you liked?
  • Johnny, the next-door neighbor, was pretty cute until he got weird.
  • You have to choose someone you saw today to go on a date, who do you choose?
  • Well, I haven’t gone anywhere today and have only seen my family, so this is awkward.
  • When was the last time you were terrified of something and screamed out loud?
  • Please don’t say a baby frog.
  • Have you ever had a crush on one of your friend’s boyfriends?
  • Do I have to answer this?!
  • Do you ever really stop to smell the roses?
  • If you haven’t, it really is a must!
  • What is something you have seen on social media that is totally cringe-worthy?
  • We know we have all seen it!
  • Give me your best “less is more” example.
  • This weird question to ask might not be the least bit weird at all and more super interesting.
  • What is one product that you absolutely love that you could sell to anyone?
  • Is it your favorite makeup brand, straightener, or maybe it is your favorite food? Tell us what it is!
  • What is the strangest thing someone has ever given you?
  • There was this one time when my boyfriend gave me a …
  • What is a little kid show that you still watch?
  • We all do it… You can’t deny the fact that you probably do it too!
  • What is your favorite Disney character?
  • 9/10 it is a princess.
  • Would you rather look like a skunk or smell like a skunk?
  • Both are equally as bad IMO.
  • Does your leg hair ever stop growing?
  • I was asking for a friend who forgot to shave.
  • Would you join pageants if your mom let you?
  • Will you be the next Miss USA?
  • What is one thing that you have learned that has helped you the most?
  • Everyone has one thing that they are so grateful that they learned how to do.
  • If you could max out all your credit cards at one store and then someone else would pay the bill, what store would it be?
  • There are so many choices…
  • Would you rather be rich, a model, or super smart?
  • You have to pick just one.
  • Would you ever want to be on reality TV? Which show would you choose?
  • She probably has big dreams to be the next Bachelorette, just saying!
  • What is the most unusual deal breaker you have?
  • The more out there, the better.
  • Which decade would you want to live in?
  • Is it the 50s, the 60s, or maybe the 80s?
  • If you could get away with committing just one crime, what would you do?
  • Everyone wishes there was just one thing they could get away with.
  • What is the craziest thing you have ever done on a whim?
  • Perhaps she has a wild side that you are attracted to.
  • Have you ever run after someone yelling for them?
  • She might laugh or cry depending on who she was chasing.
  • What is the worst pickup line you have ever said to someone?
  • Oh gosh, hopefully, it wasn’t the one she told you last week!

Weird Questions to Ask a Guy

Weird Questions to Ask A Guy
  • What is your go-to exercise routine?
  • We know that all guys have one!
  • Who taught you how to be a man?
  • Hopefully, he doesn’t say Batman.
  • What is one thing that you would do to your car if money was no object?
  • Would he lift it or add an exhaust?
  • What do you do when you are stressed?
  • Perhaps he is a cat guy and pets his little cat.
  • What is something you do or watch that you don’t want anyone to know about?
  • Maybe he is a secret fan of The Bachelor!
  • What is your preferred way to get to school/work?
  • I mean, a moped would be pretty nice!
  • What is your go-to look when it comes to your wardrobe?
  • Gucci, Target, Walmart, maybe LuLuLemon?
  • Are you happy with who you are becoming, or is there one thing that you would change?
  • This is a very telling question, if I might say so myself.
  • Can certain things in your life speak more creativity?
  • Some people are just born to create.
  • Would you rather try and fail or never really try?
  • Mind-blowing huh?
  • Do you ever feel good enough?
  • Life is about obtained perfection; are you there yet?
  • Describe your life in 10 words or less in a sentence.
  • It might be more difficult than you think.
  • When was the last time you cried?
  • Hey, emotions are good; let it out!
  • What do you think of one-night stands? Ever had one?
  • Hopefully, this is a no unless you are into that kind of thing.
  • What is one of your secrete desires?
  • Do you think he will actually tell you? Only time will tell.
  • What is the biggest lie you have ever told your dad?
  • Everyone lies at some point, right?
  • What is something you are most ashamed of?
  • There was this one time…
  • Who would come to your funeral if you were to die tomorrow?
  • If he says no one you might want to think about that.
  • What is your type?
  • Listen carefully to what he says about this one.
  • What is one of your best talents?
  • Can he really do the splits?
  • What would you do if you were the richest man in the world?
  • Would he keep it, save it, or share it with others?
  • What is the hottest thing you have ever done for a girl?
  • It’s getting a little warm in here.
  • Fame or money, what would you rather have?
  • Do I have to pick one?
  • ASre you more of a conservative or a liberal?
  • Maybe he doesn’t even follow politics or votes.
  • Have you ever punched someone in the face?
  • Do you want a fighter?

There you have it! 75 Weird questions to ask to start a conversation. What would you add to this list? Share in the comments!

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