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49 funny questions to ask a guy to make him laugh

How many times have you had the same conversation about your favorite color, food, or music? Getting to know a person shouldn’t be like filling out a form. Do you want to get to know the other person and have a good time but are afraid of running out of a good topic of conversation? It would be best if you avoided typical and boring conversations. Here are a series of funny questions to ask a guy to make him laugh.

No more clichés. No, it’s not about “what superpower would you like to have,” but real original questions.

The magic of surprising: funny questions to ask a guy

What impression do you want to make? With these funny questions, you will not only get to know another side of the other person but also make a difference. Surprise the other person with your originality.

funny questions to ask a guy to make him laugh - surprising

Being a fun person can be attractive and interesting. Besides, with these funny questions, you know where the conversation will start, but it is unpredictable to know where it will end.

  • If you had unlimited money but could spend it only on things you didn’t need, what would be the first thing you would buy? 
  • If you had to tell your life story in a fictional book, would it be a comedy, a drama, or an encyclopedia?
  • If you were making a movie about your life and the cast were always people you have already met, who would you choose to play your role, and why? 
  • When you see a car head-on, do you associate the shape with a person’s face or a character? 
  • If you could be best friends with any historical figure today, who would it be, and what would you do?
  • What do you think blind people dream about?
  • Would you rather have a bit of laughter at a funeral or not be able to stop crying at your wedding?
  • If you had gone viral as a teenager, why would it have been? 
  • What is one truth about you that seems like a lie and one lie that could seem like the truth?
  • If you were a god and a holiday was held in your honor once a year, what kind of holiday would it be?
  • Would you like your pet to be able to talk, or would it reveal too many embarrassing things about you?
  • What is something that everyone knows but you found out much later in life?
  • What was your first fictional crush?
  • What would it be if you made an animal noise every time you sneezed?
  • What song or artist are you embarrassed to admit you like?
  • If you met your version 5 years ago, would you like him?
  • Would you prefer to be super nice and less intelligent or super bright but a little too rude?
  • What song would you play if you wanted to kick everyone out of a party?
  • Are you more into dad jokes or dark humor? What’s your favorite joke?
  • What’s the most cringe-worthy thing you’ve said or done this year?
  • What would you say if your house was being robbed and you wanted to shout something random to scare the thief off?
  • What was your first fake name or email address on the internet?
  • How long have you had something expired in the fridge?
  • Do you usually imagine being in a video clip while listening to music while walking alone on the street? 
  • What death in a series or movie did you find the most absurd?
  • How do you feel ridiculous, running in flip-flops or with a backpack?

Tug of war: funny questions to ask a guy to make him laugh

It would help if you did not close yourself off to questions for the conversation to flow. The idea is to carry on a naughty chat, using these funny questions as a comfort zone and a way to avoid awkward silences. 

funny questions to ask a guy - tug of war

On the other hand, while you must listen to what he has to say (and let him beat around the bush), you should also open up. Give your answer to the questions, and reveal another side of yourself.

  • If you had your religion, how would you be prayed to?
  • When was the last time you pretended to know the lyrics to a song?
  • What would it be if you could give men’s nipples a use?
  • What would your manual say if we all had a manual of use and warning instructions?
  • Would you rather use your favorite song as an alarm clock and end up hating it, or wake up every day to a song you already hate?
  • What odd combination of two products would you buy to make the cashier at the supermarket laugh? 
  • Have you ever had a time with emo bangs or ridiculous hairstyles? If yes, I demand a picture.
  • What would you do if you went back to when you were 10 but with your current knowledge? 
  • What weird hobby or habit would you discover if we moved in together?
  • What weird flavor combination is your guilty pleasure?
  • What would your stripper’s name be? 
  • What would be the reason you were fired on your first day of work? 
  • What would it be if you could have one use for your belly button?
  • How do you think deaf people imagine voices?
  • If every continent had a personality, what would it be?
  • What super embarrassing story from when you were little does your mother always tell?
  • If you were a superhero, what would be your weak point?
  • How would we have gotten along if we had met when we were 15?

Funny questions to ask a guy to make him laugh: Let it flow

Remember, it’s all about helping the conversation flow to avoid tense moments and getting to know the other in a fun and comfortable environment. Piece of advice: These funny questions to ask a guy offer you the perfect opportunity to create inside jokes and games, fostering a special connection between you. Use them wisely.

If you’re willing to go one step further, here are some flirty “would you rather” questions to add some spice to your conversation. Have you ever asked someone one of these funny questions? How did it work? Tell us in the comments!