Funny Questions to Ask (That Make You Look Charming and Hilarious) post image

Funny Questions to Ask (That Make You Look Charming and Hilarious)

Everyone loves to laugh, that’s just a given. Humor is a great way to connect with anyone- from a guy you’re seeing to a friend to an employer. It is one of the best ways to bond and just let loose and have some fun.

Being funny comes easily to some people, and is not as easy for others. And everyone has a different scene of humor. Some people are silly, some are raw, some have a dry sense of humor, some have a perverted sense of humor, different strokes!

You don’t need to be a natural comedian to be funny. Sometimes asking the right questions can lead to some belly-aching laughter.

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

To help you connect with a guy, or anyone really, using a little laughter, we came up with a list of the best funny questions to ask. They’re pretty universal, but you should also use your judgment and tweak as needed based on your relationship and the person’s sense of humor.

These questions are open-ended enough to spark some great conversation. You can either slip these questions into a conversation or tell him you found an awesome list of funny questions to ask someone online and why don’t you give it a try?

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Quick Tips:

– Don’t force anything, that’s just awkward, like a stand up comic trying desperately to squeeze laughs out of the audience, eek.
– Be confident- it’s not what you say, it’s the way you say it that makes an impact.
– Don’t interrupt when he’s telling a funny story — interjecting and messing up someone’s flow is just the worst and can be very annoying.
– Don’t judge what he finds funny- we all have different senses of humor, just go along with it, and maybe make a joke of the fact that you don’t understand the humor, but do it in a fun way, not being mean-spirited or judgmental.
– Don’t pretend to be comfortable with something if you’re not.

MORE: 300 Conversation Starters (Rejection Proof)

Now here are the best funny questions to ask:

  • Have you ever sent a text or email to the wrong person?
  • Have you ever said hi to someone on the street thinking they were someone else?
  • Have you ever thought something that happened in a dream happened in real life?
  • What is something that comes easy to most people except you?
  • Have you ever tripped and fallen in front of a lot of people?
  • What was your biggest fashion victim moment?
  • What is your favorite random food combination?
  • What is the most random piece of trivia you know?
  • What is your go-to party trick?
  • If you could give yourself a nickname, what would it be?
  • If you could have one superpower, what would it be?
  • Is a hamburger a sandwich?
  • If you had to marry a cartoon character, who would it be and why?
  • What innocent things would your own personal version of hell include (ex – people whistling through their noses.)?
  • What is the best prank you’ve ever pulled?
  • Has a commercial ever made you cry?
  • If you could be an insect, what would you be?
  • Have you ever been caught in a lie?
  • What is something illegal that should be legal?
  • What is the most ridiculous thing you’ve ever done when drunk?
  • What is a female fashion trend that you can’t stand?
  • What is your most random pet peeve?
  • If you could lose one of your five senses, which would you give up?
  • What is one thing you do now that you’re younger self would be ashamed of?
  • What is something you wish people would stop talking about already?
  • Do you have any strange phobias?
  • Which would you rather make public? Your bank statement or your internet search history?
  • Do you have any feminine qualities?
  • What is your spirit animal?
  • Do you believe in aliens?
  • What was your last YOLO moment?
  • What is something that scared you as a kid that you laugh about today?
  • What emoji best represents you?
  • Do you have any useless skills?
  • What is your favorite movie to quote?
  • What is the worst purchase you’ve ever made?
  • What is a ridiculous common expression people use?
  • What is your biggest guilty pleasure?
  • What is the most annoying expression people use?
  • What is your go-to karaoke song?
  • What would your DJ name be?
  • What song best represents the soundtrack of your life?
  • Have you ever experienced second-hand embarrassment?
  • Do you believe in any conspiracy theories?
  • What is your most impressive dance move?
  • Would you rather be able to eat whatever you want and never gain weight, or have all the money in the world and never need to work?
  • What is the creepiest thing anyone has ever said to you?
  • What is a clever response to “what’s up?”
  • Do you have any fast food horror stories?
  • What is something you always procrastinate on?
  • Would you rather never have to wash dishes or never have to do laundry?
  • What is something you can never have enough of (aside from money!)?
  • What would you buy first if you won the lottery?
  • What is the most ridiculous lie you’ve ever told?
  • Do you have a haircut horror story?
  • What is a trend you’re embarrassed to have taken part in?
  • What is the meanest thing someone could say to another person?
  • Have you ever been pranked?
  • What is one TV show you never miss an episode of?
  • What is a TV show you’re addicted to but embarrassed to admit to watching?
  • Who is the vilest famous person?
  • When was the last time you got into a political debate on Facebook?
  • What is the most embarrassing thing people do on social media?
  • When future generations look back on our generation, what will they laugh at us for?
  • Which animal would you like to have a conversation with?
  • When was the last time you laughed so hard you cried?
  • What’s something you can’t do?
  • What is the most addicting site on the internet?
  • What makes you laugh no matter what?
  • What is the one area of life where you never seem to learn your lesson?
  • What is the most spontaneous thing you’ve ever done?
  • What was your biggest “what was I thinking?” moment?
  • Which movie or book do you think is insanely overrated?
  • What is the most trouble you’ve ever been in?
  • What is something you wish your parents had taught you at an early age?

Some Important Points About Humor

Knowing the right questions to ask is part of the equation- it’s also important to understand how humor works. Be honest about your humor- don’t pretend to find things hilarious when you don’t.

Sometimes you won’t “get” someone’s sense of humor, sometimes this doesn’t matter, sometimes it will be a deal breaker. Most guys will want a woman who appreciates their sense of humor. If you don’t, or can’t, then it just might not be a match and that’s OK.

MORE: 50 Great Questions To Ask A Guy

The most important thing is to be real. Don’t be fake or force things. This just comes across as desperate and awkward.

You can’t ever form a genuine connection if you’re coming from an un-genuine place. Compatibility is what will determine if you have a chance or not, and it can’t be faked, just like chemistry can’t be faked.

Humor is a fun way to bond and learn about someone – try to see it from that perspective instead of seeing humor as something you need to “do” in order to win someone over.

I hope this article gave you some fresh ideas for funny questions to ask a guy or anyone else. If your focus is on building a connection with a guy, there are two important moments you need to be aware of. The first is that at some point In your relationship, your man will start to pull away. You may notice him becoming more distant and less engaged. It seems like he’s losing interest in you and you worry that soon he’s going to just leave. Do you know what to do to get things back on track? If not, read this next: If He’s Pulling Away, Do This...

The next issue arises at that inevitable point when the man asks himself: Do I want to commit to this woman for the long term? The answer will determine everything. Do you know what makes a man see a woman as girlfriend/wife material? Do you know what inspires a man to commit? If not, you need to read this too: The #1 Things Men Desire in a Woman

Want more great questions? Check out these articles:

425 Amazing Truth or Dare Questions

425+ Never Have I Ever Questions: The Ultimate List

20 Cute, Amazing Question to Ask a Guy You Like

Fun Questions to Ask a Guy to Get to Know Him Better

Funny Questions to Ask a Guy or Girl


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kiss kitty

thanx alot this has helped me get my crush now we are love birds,thank you

Reply February 20, 2021, 4:05 am

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