Being funny is hard work! For most people, it doesn't come naturally. Finding or even knowing what funny questions to ask is a skill we have to learn. If you consider yourself socially awkward, don't worry, you're not alone.

In fact, you're likely part of the majority.

If you consider the most popular TV series in recent years, the funniest characters are socially awkward. The most famous of which is Sheldon Cooper from The Big Bang Theory.

Why? Because we can relate to the awkward social situations these characters find themselves in.

Sometimes, all it takes is the confidence to say something funny to break the ice. No one is expecting you to be hilerious, but at least have something more to say than a mundane comment about the weather or the infamous:

"So, do you come here often?" 🤣

In this article, we'll explore some funny questions to ask friends, guys, girls, or random people.

30 Funny Questions to Ask friends

Starting with friends is easy. Your friends will be more inclined to laugh at your silly jokes, but they'll also join in the fun, which can help build your confidence.

Your friends will also playfully insult you. Learn to take these insults as fun.

Here are 30 questions you can ask your friends. Prepare your own answers to these questions so you can laugh at each other.

  1. What is your favorite breakup music?
  2. What's the closest you have ever come to being arrested?
  3. Who is your celebrity crush?
  4. Who was the last person you sent a text to, and what did it say?
  5. If you could define yourself in one hashtag, what would it be and why?
  6. What is your favorite song to sing in the shower?
  7. Do you think you're going to heaven or hell?
  8. What is the strangest food or drink you enjoy?
  9. If you could travel forward or backward in time, where would you go and why?
  10. What is the first thing you would do if you become a billionaire?
  11. Would you rather be put in shark-infested waters or in the bush surrounded by lions?
  12. What would you do if you only had a week to live?
  13. Do you think dentists go to other dentists, or they just do it themselves?
  14. If someone with braces dies, do you think they get buried with braces?
  15. What is your worst nightmare?
  16. Would you rather order the killing of ten humans? So, someone else will do the dirty work. Or, you have to strangle one puppy to death?
  17. What is your favorite food to eat when you're drunk or stoned?
  18. If you were only allowed to keep one of your senses, which would it be and why?
  19. For a billion dollars, you have to spend 10 minutes in a cage with a tiger. What's your strategy to survive?
  20. What is your spirit animal, and why?
  21. What nursery rhyme do you know the lyrics to?
  22. You catch your mother and partner from falling off of a cliff. To save one, you have to left the other go. Which do you choose?
  23. Which politician do you most resemble, and why?
  24. If you had to remove a letter from the English alphabet, which letter would it be, and why? Secondly, how would it affect words?
  25. Which (insert favorite TV series - for example, Big Bang Theory) character are you?
  26. Would you rather have no arms or no legs?
  27. If you had to marry one of your ex-partners to save the world, who would it be?
  28. The world is about to end, you can only choose one last pleasure. Sex with your partner/crush, or any food in the world.
  29. How do you stalk the most on social media?
  30. When was the last time you were on a dating site?

You can ask these funny questions to friends and make them laugh really hard!

30 Funny Questions to ask someone random or people you just met

Meeting new people can be hard work. But all it takes is a fun random question to ask someone, and you're bound to start a conversation.

Random funny questions will often catch people off guard, increasing the likelihood they'll want to engage with you.

The secret is not to walk up to someone and ask them these questions straightaway. This might come across as too random!

Practice working up to these questions. For example, if you're going to ask,

"What song are you embarrassed to admit to listening to?"

Start by asking,

"what music are you into?"

When they answer and ask you what music you're into, name your favorite artists but then add something like,

"And, I also love that Justin Bieber song Baby. But I don't usually admit it. What song are you embarrassed to admit to listening to?"

Get the picture? Good 😉.

  1. Do you have a tattoo? If yes, how many and where do you have them?
  2. What is the crime you would commit if it were legal for a day?
  3. What song are you embarrassed to admit to listening to?
  4. Which three celebrities would you kiss, marry, or kill?
  5. What is your favorite song when you are high?
  6. What is your middle name?
  7. Why do they call it 'drive-through' when you have to stop?
  8. What is your most embarrassing childhood memory?
  9. If you were allowed to eat only one food for your whole life, which one would you choose?
  10. Have you ever been arrested?
  11. Why do you think they use a sterile needle to death by lethal injection?
  12. What did you want to be when you were five?
  13. What's the first thing you would do if you become a billionaire today?
  14. If you could live the life of any movie character, which one would it be and why?
  15. If you could be any superhero, who would you be and why?
  16. Would you go to Mars if it meant you couldn't return?
  17. What's the worst movie you have ever seen?
  18. If you won a week's vacation to anywhere in the world, where would you go and why?
  19. Would you rather be a famous musician/rock star or a famous actor?
  20. Do you think they should legalize drugs?
  21. What's the craziest religion?
  22. What's the craziest thing you have ever done (like skydiving, bungee jumping, etc.)?
  23. Have you ever had to lie for your best friend?
  24. Which three people would you choose to be stranded on a deserted island with?
  25. What's the funniest thing that's ever happened while traveling or on holiday?
  26. What's the most random comment you have received on a social media post?
  27. What are some of the most random funny questions you have been asked by strangers on social media?
  28. Do your parents ever comment on your social media posts? What's the funniest or most embarrassing thing they have posted?
  29. What's the craziest thing you have done when you were wasted?
  30. Why is water wet?

These 30 are no doubt awesome funny questions to ask someone random. Give them a try.

30 Questions to ask a girl

Are you looking to mess with your girlfriend, and know things about her at the same time? Or, are you looking to spend time with your girlfriends, asking fun and random questions? Take a look at my list of 30 random and funny questions to ask a girl or a lady in general.

  1. Who was your first crush?
  2. If you could change something about yourself, what would you change and why?
  3. Who is your favorite celebrity crush and why?
  4. What do you prefer in boys, cute or hot?
  5. What were you like as a kid?
  6. How did you meet your first boyfriend or girlfriend?
  7. What is your favorite curse word?
  8. What is one weird thing that turns you on?
  9. What are two things that you hate and love about boys?
  10. Would you rather be, very clever or very beautiful?
  11. What is your dream house like?
  12. What do you prefer, smart boys or handsome boys?
  13. Do you believe in true love? Is yes, what do you think true love is? If no, why not?
  14. Do you like to read? If so, what is your favorite book?
  15. If you were to marry the last person you kissed, would you be happy?
  16. How many relationships have you had?
  17. Have you lost anyone loved?
  18. What is your favorite thing to do in your free time?
  19. What do you love more, books or movies?
  20. What is your fighting style, drunken monkey or angry monkey?
  21. Have you ever been in a fight with your best friend? Is yes, why? If no, would you like to?
  22. Have you ever been cheated on, and hurt by somebody you love? What did you feel about it and what do you think would you do in future to prevent it?
  23. What is your color and why?
  24. What kind of dresses do you prefer, stylish or comfortable? Why?
  25. On a scale of 1-10, how fashion conscious do you think you are? Do you think fashion consciousness really matter?
  26. On a scale of 1-10, how much do you love your boyfriend (or love me, if she is your girlfriend)?
  27. Who do you think are more trustworthy, boys or girls? Why do you think they are more trustworthy than one another?
  28. What is the worst memory you had of your childhood?
  29. If you had to choose only one, who would you choose; your soulmate or your family?
  30. Which of your friends do you think is jealous of you? And, how do you feel about it?

30 Funny Questions to ask a guy

Men, on the surface, seem like an alien, weird and stable creatures to girls. But, in reality, they are just a ball of an emotional mess like girls, and love funny question answers.

During my time asking questions from boys, I found that boys are more quirky and funny at giving answers. But, you have to know the right questions to crack their shell of attitude, and reveal their fun and emotional side. With the right questions, you can make them startled and feel intimidated by questions. So, here it is- the list of 30 funny questions to ask a guy.

  1. What is your favorite sport and why?
  2. Have you ever kissed a guy? If yes, how do you feel about that?
  3. Have you ever had hots for your friend's girlfriend?
  4. Have you ever cheated in a relationship? If yes, did you tell your girlfriend and how did you feel about that?
  5. Who was your childhood hero?
  6. What kind of music do you listen to?
  7. What is one thing that inspires you?
  8. What is your favorite midnight snack?
  9. If you had to choose only one, which one would you choose; sex or food?
  10. Would you be happy if you married the last person you had sex with?
  11. What do you prefer, movies or video games?
  12. Have you ever been in a true love? Or, do you believe in true love?
  13. If you were the last living human in the world and you lost both your hands, how do you think would you masturbate?
  14. Who do you think is a better superhero, Batman or Superman? Why?
  15. If you were allowed to change one event in your life, which one would you choose?
  16. Who is your favorite superhero and superpower, why?
  17. Who do you think is a better player, Ronaldo or Messi?
  18. Do you think you can live in a world without girls? Why?
  19. Do you believe in zodiac signs? If yes, what is your zodiac sign?
  20. What is your deepest and darkest secret?
  21. Have you ever had any nicknames? What were those names?
  22. Do you ever think about the meaning of life? What do you think it is?
  23. Imagine that you are on a crashing plane with 100 most important people in the world and you get to save only three of them, which three would you save?
  24. If you had the power to bring back any one dead musician, which one would you bring back and why?
  25. If you had a teleportation machine, where would you go and why?
  26. Imagine you had a chance to remove TV shows and movies you don't like, which 10 movies and TV series would you remove from the face of the planet?
  27. If I had two pills, one pill for unlimited happiness and another for unlimited wealth; which one would you take? Why?
  28. If you were born in the eighteenth century, how different do you think your life would be? Do you think you could live in that century without all this technology at hand?
  29. What do you prefer, smart girls or hot girls?
  30. If you could live the life as any celebrity, whom would you choose?