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51 Funny Questions To Ask a Guy Guaranteed To Make Him Laugh

A photo of Tom who is the Co-Founder of Questions About Everything

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These funny questions to ask a guy are perfect if you want to lighten the conversation and get a feel for his sense of humor.

We’ve put together a great list of funny questions to ask guys you can use to lighten the mood in any conversation. They should make him laugh and open up a bit more too.

Some of these are dumb questions to ask a guy while others are a bit more introspective and focus on their past, which will give you an indication of their personality and what they’re like.

So if you’re looking for some hilarious questions to ask guys, check out the ones below and use them in your next conversation with the guy in your life!

Funny Questions To Ask a Guy List

funny question to ask a guy on whether they've said something to someone they shouldn't have
  • Have you ever put your foot in your mouth and said something you shouldn’t have? If so, what happened?
  • Who would win in a fight between a polar bear and a leopard?
  • What’s the most embarrassing thing that’s happened to you in public?
  • What food combination, such as pineapple on pizza, do you think is an abomination?
  • What’s the funniest thing that happened while you were in high school?
  • Have you ever injured yourself in a stupid way?
  • What would you come back as if you could be reincarnated as an animal?
  • Is there one expression everyone uses that really grinds your gears?
  • What’s the silliest thing that really winds you up?
  • Have you ever set the kitchen on fire while you’ve been cooking?

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  • Have you ever used a really cheesy chat up line and been successful?
  • What’s the funniest insult you’ve ever heard?
  • Have you ever overheard a conversation that had you in stitches?
  • If animals could talk, which one do you think would be the funniest?
  • What’s the worst possible superpower anyone could have?
  • What’s the silliest thing you’ve ever seen happen while you were at work?
  • Do you shower facing towards the water or away from it?
  • What’s the strangest habit you had as a child?
  • If you were a professional wrestler/boxer, what would be your walkout theme?
  • What’s the one piece of junk food you can’t resist?
funny question to ask a man on the one piece of junk food they can't resist

Next: Random Questions To Ask a Guy

  • What’s the best prank you’ve ever pulled on someone?
  • What’s the most bizarre item that you think would be useful in a zombie apocalypse?
  • If you were forced to take part in a reality TV show, which one would you choose?
  • When was the last time you laughed so hard you started crying?
  • What’s the worst fancy dress costume you’ve ever seen?
  • How many beavers would it take to bring down a rhino?
  • What sport would be more entertaining if drinking beer was mandatory while it was played?
  • What Disney film do you secretly enjoy?
  • What’s the most ridiculous word you’ve ever used in a sentence without anyone noticing?
  • Would you rather have three arms or three eyes?
  • Which cartoon character would you love to swap places with?
  • What’s the weirdest dream you’ve ever had?
  • What’s your spirit animal?
  • What’s the longest you’ve worn the same pair of underwear?
  • Why is the plural of sheep, not sheeps?
  • Have you ever been caught dancing or singing in front of a mirror?
  • What’s the stupidest thing you’ve done while drunk?
  • Who’s your favorite comedian?
  • What are your guilty pleasures?
  • Have you ever made a prank call? If so, who was it to and what happened?
funny question to ask guys on whether they've ever made a prank call before

You might also like: Questions To Ask a Guy

  • Is there a movie that everyone thinks is rubbish that you enjoy?
  • What’s the most mischievous thing you did as a child?
  • Do you secretly wish pokemon were real?
  • What’s the worst joke you know?
  • What fictional character do you secretly find attractive?
  • What’s the most bizarre fact you know?
  • What’s your quirkiest trait?
  • Have you ever been caught doing something you shouldn’t have been?
  • If you could be a fly on the wall, whose wall would you be a fly on?
  • Do you have a secret skill no one knows about? What is it?
  • What’s the silliest thing guys wish girls knew about them?

Looking For More Questions?

Questions Girls Are Afraid To Ask Guys – A collection of questions you’ve been dying to ask the guy in your life.

Questions To Ask Your Crush – Got a crush on a cute guy? Here are some questions you should ask him!

Funny First Date Questions – Going on a first date and want some questions to lighten the mood? We’ve got you covered!

Funny Conversation Starters – A great set of questions if you’re still looking to make him laugh.

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.