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This post is all about funny questions to ask a guy.

funny questions to ask a guy

Let's be real, guys love hilarious conversations. But, it can often be hard to think of things to make them laugh.

These funny questions to ask a guy are the perfect thing to pull out when out to dinner with your man (it will lead to the BEST conversations) or just late at night when you guys are texting. It's also the perfect conversation starter if you don't know what to talk about.

I love having these saved to my phone so when we go to dinner I can pull them up and start asking my boyfriend questions. One question leads into so many more questions and it turns into the best conversations!

This post shows you 100 funny questions to ask a guy.


  • What was the funniest/most embarrassing moment you had as a kid?
  • What is the most funny scene you have seen in a movie?
  • What would be the scariest sound you would hear after suddenly waking up in the middle of the night?
  • What is the sexiest and least sexist name?
  • What is the funniest joke you can think of right now?
  • If you had to become an inanimate object for a year, what would you become?
  • Who is you nemesis and why?
  • What sport would be the funniest to add a required alcohol consumption too?
  • If your life had a theme song, what would it be?
  • If you were a DJ, what would your DJ name be?
  • What is the best and worst thing about being a male?
  • What is something that everybody looks stupid doing?
  • If you were suddenly put into a 5-year-old body, what would you do first?
  • What is something funny that I wouldn't believe about you?
  • What is the most iconic way someone could die?
  • What childish thing do you still enjoy?
  • What is the one thing people will look back at that's popular now and think. "What the h*ll were we doing?!"?
  • What reality TV show would you most likely be in?
  • What long shot did you take that really paid off?
  • If animals could talk what would be the rudest?
  • What do you think you would be doing if you never had to work in your life?
  • You are about to get in a fight, what soundtrack comes on?
  • What movie do you wish your life was like?
  • In 40 years, what will people miss?
  • If you managed to survive the apocalypse would be your post-apocalypse job?
  • What celebrity would make the worst leader of our country?
  • What would be the coolest animal to size up to a horse?
  • What came first, the egg or the chicken?
  • Do you consider yourself more of a nice person or a naughty person?
  • What are three things you would never spend your money on?
  • Is it better to be a man or a woman?
  • What's the craziest/most illegal thing you have ever done?
  • Do vegetarians eat animal crackers?
  • When I erase a word with a pencil, where does it go?
  • Why doesn't glue stick to the inside of the bottle?
  • Why was the alphabet placed in the order it was?
  • What is someone you say you will do, but won't actually ever do it?
  • What is the last thing you searched for on your phone?
  • If you had to choose between going naked or having your thoughts appear in thought bubbles above your head for everyone to read, which would you choose?
  • What is the first thing you would do if you woke one day as the opposite sex?
  • Of all the people in the world, who would you most want to trade lives with?
  • What would be in your web history that you would be embarrassed if someone saw?
  • Would you rather lose your sex organs forever or gain 200 pounds?
  • If you were reborn, what decade would you be born in?
  • The world ends next week and you can do anything you want (even if it's illegal). What would you do?
  • What ‘As seen on TV’ product do you secretly want to buy?
  • What is something you’ve done to try to be ‘cooler’?
  • Who would you hate to see naked?
  • What's the longest you have gone without a shower?
  • If you could text one person for the rest of your life but never see their face, who would it be?
  • What is one thing you would never eat on a first date?
  • If you could only use one swear for the rest of your life, what would it be?
  • Would you rather not shower for a month or eat the same meal for a month?
  • What is the worst gift you have ever received?
  • If you could choose to never sweat for the rest of your life or never have to use the bathroom, what would you choose?
  • Have you ever stalked someone on social media?
  • If you could change anything about your life, what would you choose?
  • If you could take a place of any guy in the world, who would you choose?
  • What would you do/not do for a million dollars?
  • If you could do one thing for the rest of your life what would it be?
  • What is the worst movie you have ever seen?
  • What is the weirdest thing you used to do as a child?
  • What is the most historic event you have either witnessed or taken part in?
  • What do you consider your best talent?
  • If you could have any animal as a tame pet what would you choose?
  • What would you consider the most important thing you have done in your life?
  • What has been your biggest kitchen fail?
  • If you could kill any character from a television show, who would it be?
  • If you could create a holiday, what would it be?
  • What set of items could you buy that would make the cashier most uncomfortable?
  • What was the funniest prank you have ever pulled?
  • What's the most cringe-worthy thing you have seen on social media?
  • What do you have a hard time with that most people find easy?
  • What was the worst purchase you have ever made?
  • What is the grossest thing you have ever eaten?
  • If you could have a super power, what would it be?
  • If you could drink with any historical figure, who would it be?
  • If you could have any job you wanted and salary wasn't an option, what job would you choose?
  • If you had to sing one song in front of a stadium, what song would it be?
  • What movie was so sad you will never watch it again?
  • What do you most look forward to about getting old?
  • If you could drop anything and go on a trip somewhere, where would you go?
  • What makes you angrier than it should?
  • What is the manliest and least manly thing you have ever done?
  • What is your favorite physical attribute about yourself?
  • What's one thing you want to ask a women but are too scared to?
  • If you had to describe me to a stranger what would you say?
  • How did you get your first kiss?
  • What is the funniest thing you have ever done or said?
  • Have you ever been caught naked by someone?
  • If you could read minds who would you want to read?
  • How do you handle people you don't like?
  • Would you spit in a persons food if they were being rude to you?
  • Are you superstitious? If so, what are you superstitious about?
  • How would you describe yourself in three words?
  • What is your biggest regret in life so far?
  • If you HAD to get plastic surgery somewhere on your body, what would you change?
  • Of all your pet-peeves, which is the strangest?
  • If you inherited or won a million dollars, what would you do with it?

That post gave you 100 funny questions to ask a guy.

One Comment

  1. Hey there! I’ve been reading your blog for some time now and finally got the courage to go ahead and give you a shout out from New Caney Texas! Just wanted to tell you keep up the fantastic job!

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