100 Funny Icebreaker Questions

icebreaker, questions, activities, groups, funny, humorous, laughSocial situations don't have to be awkward. Avoid the long periods of silence by asking fun questions to get people talking. Icebreaker questions are the perfect way to start meetings, initiate conversations and to get people talking in any setting. 

Once you've got the conversational ball rolling, this will put people around you at ease. Icebreaker questions are also a great way to improve connection with people. Simple questions allow you to discover fun, silly or even interesting facts about people.  

So, whether you are at a dinner party with people you just met, waiting for a meeting at work to begin, or leading a group event - this list of fun icebreaker questions is a great way to change the vibe in the room and to fill the air with fun stories, interesting facts and even some laughter. There are many opportunities in life where you need to converse with people you don't know very well, so here are 100 funny icebreaker questions to really get the conversation rolling!

Funny Throwback Questions About Your Past

Get people sharing fun stories about their childhood or growing up. Stories are a great way to connect with other people and get them sharing information about their life. Plus, it's likely that people will relate to some of the stories and experiences which is guaranteed to build relationships with people in the group.

  1. What are your favorite songs from your teenage years that you still rock out to when nobody else is listening?
  2. Who was your childhood actor/actress crush?
  3. What's your most embarrassing moment from your teen years?
  4. What's the craziest dare you ever took?
  5. What's the grossest food you ever had to eat to be polite?
  6. What's the worst thing you ever did as a kid — and got away with?
  7. What's the craziest fashion trend you ever rocked?
  8. What did you get into the most trouble for with your parents as a kid?
  9. What's your silliest memory with your best friend?
  10. What part of elementary school do you wish you could incorporate into your adult life? (i.e. naptime)
  11. What was the first concert you ever went to?
  12. Do you have any crazy roommate stories?
  13. What is the weirdest thing you've ever eaten for breakfast that is not a breakfast food?
  14. What's the strangest family tradition in your family?
  15. What was your favorite item of clothing as a kid?
  16. What did you name your first car?
  17. What Disney/cartoon character were you inexplicably afraid of as a kid?
  18. What was your first record, tape or CD that you ever owned?
  19. What were words you couldn't pronounce as a child, so you made up your own?
  20. Have you ever gotten super lost? What happened?

  1. What's the story of your first crush?
  2. What was your first job? What did you like/dislike about it?
  3. Who was the worst grade-school teacher you ever had?
  4. What afterschool activity did you quit as a kid, and why?
  5. What's the funniest thing that ever happened on your family vacation?
  6. What's the funniest animal you've ever owned as a pet?
  7. What's the worst haircut you ever had?
  8. What's the best prank you've ever played on someone?
  9. What's the most ridiculous thing your parents ever did to embarrass you?
  10. As a kid, did you ever do something wrong but manage to pin it on your siblings?
  11. What's the worst job you've ever had?
  12. What totally rad expression did you overuse in high school?
  13. What was your favorite Halloween costume you wore as a child?

Fun Facts About Yourself

Almost everyone enjoys talking about themselves. Fun questions that ask people to share facts and stories about themselves are easy, sometimes funny and a great way to make things enjoyable. Not everyone enjoys talking in a group, but almost everyone enjoys talking about themselves. So, give these questions a try when you've got a quiet group and need to brighten the mood of the room.

  1. Who is your craziest/most interesting relative?
  2. What band would you be embarrassed to admit you listen to?
  3. What's the craziest thing on your bucket list?
  4. What's a weird fact you happen to know?
  5. What is your real favorite movie, and what movie do you pretend is your favorite to sound cultured?
  6. What's your strangest talent?
  7. What's your funniest talent? Or un-talent?
  8. What's your best idea for a reality TV show?
  9. Which Disney character's story does your life most resemble?
  10. Everyone has those recurring bad dreams … what is your nightmare?
  11. What are two truths and a lie about you?
  12. What's a funny (appropriate) pick-up line that works for you?
  13. What's your favorite part of a county fair?
  14. What show on Netflix did you binge watch embarrassingly fast?
  15. Which celebrity do you shamelessly follow in the news?
  16. What's something about you that people would be surprised to know?
  17. What is your favorite smell and why?

  1. What's the best knock-knock joke you know?
  2. What completely safe animal are you inexplicably afraid of?
  3. What food could you not live without?
  4. What dance move are you secretly awesome at?
  5. What commercial jingle gets stuck in your head all the time?
  6. What sport did you try as a child and fail at?
  7. What interesting skill do you want to learn?
  8. What's the most random thing in your purse/wallet?
  9. What invention do you think will be popular in 20 years?
  10. What blog or website are you embarrassed to admit you love?
  11. What do you never leave the house without (can't be your phone, keys or wallet)?
  12. Who is your celebrity look-alike?
  13. What's your real favorite book, and what book do you pretend is your favorite to sound smart?
  14. What do you pretend to hate but actually love?
  15. What's a nickname people actually call you?
  16. If you could pick your nickname, what would people call you?
  17. Have you ever lied about an interest/talent to impress someone? What happened next?

Fun Hypothetical Questions

Hypothetical questions are downright fun. There's no right or wrong answer. These types of questions are especially fun with middle and high school aged students. So, if you are a teacher, coach or youth leader - you might want to try some of these questions at your next youth event to help everyone feel connected and engaged.

  1. If you were famous, what would you be famous for?
  2. If you had a boat, what would you name it?
  3. If you could pick a TV show to be your life, what show would it be?
  4. If your best friend picked a tattoo for you to get, what would he/she pick?
  5. If you could only eat at one restaurant forever, what restaurant would it be?
  6. If you could only wear one type of shoes for the rest of your life, what type of shoes would it be?
  7. If you could have any celebrity be your best friend, which celebrity would you pick?
  8. If you created your own country, what would it be called?
  9. If all your clothes had to be one color forever, what color would you pick?
  10. If you had to be an animal, which animal would you be?
  11. If you had lots of money, what unnecessary thing would you splurge on (i.e. a private plane, concert tickets)?
  12. If you could switch places with anyone in your family for a day, who would it be?
  13. If you wrote a book, what would it be called?
  14. If you had to use a fake name, what fake name would you make up?
  15. If you could live any historical figure's life, which one would you choose?
  16. If you could eliminate one food so that no one would eat it ever again, what would you pick to destroy?
  17. If you had to wear a hat every day for the rest of your life, what type of hat would it be?
  18. If you could create one holiday, what would you create?
  19. If you were a vegetable, what would you be?
  20. If you were an Olympic athlete, what sport would you compete in?
  21. If you were the president, what would you change about the decorations in the White House?

  1. If you were a type of jeans, what type would you be?
  2. If you could be one superhero, which superhero would you be?
  3. If you could turn the ocean into a liquid other than water, which one would you pick?
  4. If you had to be Siamese twins with one person, which person would you pick to be stuck with?
  5. If you could pick three famous people to be a part of your entourage, who would you pick?
  6. If you could only listen to one song for the rest of your life, which song would you pick?
  7. Which celebrity would you pick to exchange lives with?
  8. If you could pick one job to do forever (and be guaranteed all the money you need), what job would it be?
  9. If you were trying out for a singing reality show, what song would you sing?
  10. What game show would you be super awesome at?
  11. If you had to endorse a brand, which brand would it be?
  12. Last and possibly least … The corniest icebreaker question ever: How much does a polar bear weigh? (Just enough to break the ice!)
So, be the conversational hero at your next club, group or workplace meeting. Use this list of helpful questions to help break through the awkward silence and start some fun conversations!

Kayla Rutledge is a college student who spends most of her time writing, singing for her church and eating quesadillas.

Additional Resources

Icebreaker Questions for Small Groups

Icebreaker Activities for Any Group

Icebreakers for Youth Groups

Quick Icebreakers for Work Meetings

Icebreakers for School