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Icebreakers are an effective way to get to know people you meet at a party and deepen connections with coworkers. They can be used in one-on-one situations and small and larger groups. 

Here are 228 icebreaker questions to help you build an authentic connection with coworkers, friends, and strangers you’d like to know better. 

Deeper Get-to-Know-You Questions

When you’re with people you’ve known for a while or want to take a relationship deeper, think about including some of these questions in your conversation.

  1. What is your biggest regret?
  2. What would you call your most significant achievement?
  3. When in life have you felt most alone?
  4. When have you felt most alive?
  5. What is your favorite story about your parent?
  6. What year would you like to do over?
  7. What is your earliest memory?
  8. Who is one of the people you most admire and why?
  9. What book impacted you the most?
  10. If you could pick a decade to visit on a time machine, what would it be?
  11. Do you get along with your siblings?
  12. Have you ever considered a different career?
  13. What was your first boss like?
  14. Who is the first person you go to when you need comfort?
  15. What do you hope your descendants know about you?
  16. What is your favorite quote?
  17. What was the best year of your life?
  18. Have you ever considered writing a book?
  19. What’s your hidden talent?
  20. What’s something most people don’t know about you?
  21. What is the longest project you have ever worked on?
  22. Tell me your most embarrassing work story.
  23. What’s the best advice you’d give someone in their first job?
  24. What is a non-negotiable in your daily routine?
  25. Who is the first person you go to when you need comfort?
  26. What do you hope your descendants know about you?
  27. What sandwich best represents the layers of your life?
  28. Has there been a movie that touched you so profoundly you cried?
  29. What is your favorite quote?
  30. What year would you like to do over?
  31. What was the best year of your life?

Find 60 Fun And Exciting Virtual Icebreakers For Remote Work to keep you and your coworkers or friends in faraway places connected.

Questions to Ask About Hobbies

Another way to get to know people is to learn about what they do for fun during their free time. Asking questions about hobbies helps you find shared interests and set the stage for meaningful conversations.

  1. What is your favorite thing to do in your free time?
  2. What is the strangest hobby you’ve ever had?
  3. Have you ever lost a relationship because of a hobby?
  4. Who influenced your interest in your hobby?
  5. Who is your favorite writer?
  6. Have you ever considered writing a book?
  7. If you could win a gold medal in any sport, what would it be?
  8. Do you have any family members that are notable in their hobbies?
  9. Did you ever collect stamps as a child?
  10. Tell me about a significant moment you had on stage.
  11. What are some of your unique talents?
  12. Are you an artist, a singer, a comedian, or an athlete?
  13. How far back can you trace your family history?
  14. What’s your hidden talent?
  15. What musical instrument do you play—or wish you did?
  16. What tips would you give to someone learning to [hobby]?
  17. Has there ever been a time you thought about quitting?
  18. Have you ever been injured doing your hobby?
  19. Who is the GOAT of [hobby], and what would you ask them if you had the opportunity?
  20. What’s the funniest thing that’s happened while doing [hobby]?

Icebreaker Dares

Great conversation starters help people feel more relaxed and encourage conversation and laughter. They also bring a personal touch to whatever environment you’re in.

  1. Tell us about the last dream you can remember.
  2. Do an impression of your favorite celebrity.
  3. What is your favorite movie that you secretly know is actually terrible?
  4. Share your worst habit.
  5. Have you ever bribed or flirted with a police officer to get out of a ticket?
  6. What is something you most look forward to doing when you retire?
  7. What is one thing you are constantly losing?
  8. What is the strangest thing you have ever bought?
  9. Do you have a weird collection? If so, what?
  10. Tell us about the last dream you can remember.
  11. If you could do one thing you did when you were a child, what would it be?
  12. Have you ever danced on a table when you were drunk?
  13. Have you ever told someone you wouldn’t be home just so they wouldn’t come over to yours?
  14. What is the one thing you dislike about yourself?
  15. What is the one thing you really like about yourself?
  16. What is the one thing you would stand in line for?
  17. What is the nicest compliment you’ve ever received?
  18. Have you ever lied on your resume to get a job?
  19. If anyone in your family could win an award for being the most annoying, who would it be?
  20. What was the most embarrassing thing that you ever did while on a date?
  21. What was the worst gift you ever received?
  22. What is the one thing you are the most afraid of?
  23. What talent are you most proud of?
  24. What was the one thing you could never learn how to do no matter how hard you tried?
  25. What is something you find absolutely disgusting to the point you get sick?
  26. Do you sing in the shower when you think no one is listening?
  27. Do you clean your house before the housekeeper comes?
  28. What reality TV show should you be on?
  29. What part of your morning routine is the most important?
  30. What actor would you most like to date?
  31. What vegetable most resembles your state of mind?
  32. What’s your biggest regret? 

Funny Icebreaker Questions About Childhood

Stories of youth can quickly bring laughter and common ground to any situation. After all, there’s nothing better than finding someone else who was a Beanie Baby fanatic or sported a bowl haircut. Consider asking one of these icebreakers:

  1. How did your parents choose your name?
  2. What teacher did you have a crush on?
  3. What fad did you embrace while growing up?
  4. Did you have any nicknames as a child?
  5. Did you have to walk uphill both ways in the snow to get to school?
  6. What was the dumbest thing you did to try to impress your crush?
  7. Were you the last picked or the first picked in recess games?
  8. What was the most rebellious thing you did as a child?
  9. Did you ever try to eat a non-food item?
  10. What did you wear when you were younger that mortifies you now?
  11. Are you still friends with any of your grade school classmates?
  12. What advice should you have taken from your parents?
  13. What was your favorite cartoon?
  14. Did you ever sleep with a doll or stuffed animal?
  15. Did you and your siblings fight?
  16. Who was the most influential public figure as a kid?
  17. Were you a spender or a saver as a child?
  18. What was the best thing you ever bought with your own money?
  19. Did you have a special fort or hiding place?
  20. What was the strangest thing you wanted to be when you grew up?
  21. Tell me about the best field trip you ever took.
  22. How long did you believe in Santa?
  23. Was there a story or fairytale that scared you as a child?
  24. What was your favorite song?
  25. Where was your first kiss?
  26. Did you have an unusual pet?
  27. What was your favorite joke as a kid?
  28. What tv show character did you want to be?
  29. What dish on your family’s table did you most look forward to?
  30. What was the first album you purchased?
  31. Did you fear being abducted by aliens?
  32. What was your least favorite food that you now enjoy? 

Never Have I Ever Questions

Never Have I Ever is a super simple game that can be adapted to any situation—with peers, colleagues, family, and children. This is how it works: each person shares a statement about something they’ve never done. Anyone who has done that thing has to respond by either putting a finger down or taking a sip of their drink.

Regardless of how you play, you may learn something surprising about what your friends (or coworkers) have done. 

  1. Peed in the pool
  2. Laughed so hard you spit out your drink
  3. Gotten fired
  4. Done the walk of shame
  5. Been homeless
  6. Gotten a pedicure
  7. Been to the emergency room as a patient
  8. Been unemployed
  9. Used an emoji
  10. Gotten detention
  11. Been caught in a lie at work
  12. Received a speeding ticket
  13. Gotten a tattoo
  14. Slept in your car overnight
  15. Kept a library book
  16. Cheated on a test
  17. Run from the police
  18. Been drunk
  19. Dined and ditched
  20. Responded to a booty call
  21. Drunk texted
  22. Called in sick when I wasn’t
  23. Been grounded
  24. Gone to a strip club
  25. Revealed a family secret
  26. Wet the bed
  27. Burped on a date
  28. Ghosted someone
  29. Been ghosted
  30. Quit a job
  31. Had toilet paper hanging out the back of my pants
  32. Lost my keys when they were in my hand
  33. Danced on a table
  34. Vomited after a workout
  35. Broke someone’s heart
  36. Had my heart broken
  37. Been to the opera
  38. Received flowers from a date
  39. Kissed someone at midnight on New Year’s Eve
  40. Worn a tuxedo
  41. Been in a limousine
  42. Eloped
  43. Been thrown out of a library
  44. Cheated on my partner
  45. Shared chewing gum with anyone
  46. Sent an inappropriate text to your boss by accident
  47. Bought something to wear to an event and then returned it
  48. Fallen asleep in church
  49. Broken up with someone just before a holiday so that you didn’t have to buy them a gift
  50. Snuck into a movie while underage
  51. Caused a car accident
  52. Forgotten a wedding anniversary
  53. Been arrested
  54. Gotten a speeding ticket
  55. Been stuck in an elevator
  56. Owned a pet snake
  57. Shoplifted
  58. Fainted
  59. Done karaoke
  60. Pulled an all-nighter for work
  61. Had a crush on a relative
  62. Met a celebrity
  63. Gotten so sunburned that the skin peeled
  64. Seen a rainbow
  65. Made a snow angel
  66. Found a four-leaf clover

Find an additional 301 Never Have I Ever questions to spice up your next gathering. 

Best Icebreaker Questions for Road Trips

During long hours on the road or en route during travel, use the time to get to know your companions better. You may want to use this list of icebreaker questions as a reference to keep the conversation interesting and engaging.

  1. Did you ever take any great road trips?
  2. What was the most meaningful experience you’ve had while traveling?
  3. What was your best vacation?
  4. Do you have a travel-related bucket list item?
  5. Are you a member of the mile-high club?
  6. Have you ever been carsick?
  7. Have you been outside the country?
  8. Do you speak another language fluently?
  9. Do you prefer to have a detailed itinerary or see where your interests lead?
  10. Do you like traveling with someone else or alone?
  11. What’s your idea of the perfect vacation?
  12. Where would you like to travel next?
  13. Would you go bungee jumping?
  14. Mountains or beach?
  15. Have you ridden on a train?
  16. Was there a movie or book that inspired one of your trips?
  17. What is your favorite place to relax?
  18. What’s the best place to hike?
  19. What’s your favorite way to travel?
  20. If you could, would you sign up for space travel?
  21. Would you rather spend a year alone on a deserted island or in the most populated city on earth? 

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Would You Rather Conversation Questions

Asking hypothetical questions is another conversation game to add to an evening out with friends or an office meeting. It is super simple, takes very little time, and can be done almost anywhere. It works by asking a series of questions with two options.

  1. Be a celebrity that is followed around 24/7 or stay under the radar for your whole life?
  2. Be an ant or an elephant?
  3. Win the lottery or a Nobel prize?
  4. Surf the web or surf the waves?
  5. Be the queen bee or the king of the herd?
  6. Be comfortable for every day of the rest of your life or have one phenomenal day every year and struggle the rest of the time?
  7. An Olympic gold medalist or an astronaut?
  8. Speak all human languages or be able to talk to all animals?
  9. Run at 100 miles per hour or fly at 10 miles per hour?
  10. Give up your smartphone or your hearing?
  11. Keep your looks or your mind?
  12. Really tall or really short?
  13. Be hairy or completely bald?
  14. Have a personal chef or a personal assistant?
  15. Know the future or change the past?
  16. Trick-or-treat as a kid or as an adult with your kids?
  17. Prefer to work out indoors or out?
  18. If you could have any view from your office window, what would you choose?
  19. Return to childhood or jump to retirement?
  20. If you got to pick your name, what would it be?
  21. If you were the ruler of the world, what problem would you solve first?
  22. Be liked or respected?
  23. If you could only eat one item for every meal for the rest of your life, what would it be?
  24. Stay up all night or sleep all day?
  25. See the world up close or from space?
  26. Interview a politician or a celebrity?
  27. Walk on the moon or fly?
  28. Be a Disney character or a Marvel character?

Don’t miss these 246 Would You Rather Questions For a Fun Game Night to amp up your conversation repertoire.

Final Thoughts

Getting to know people doesn’t have to be intimidating when you have some ideas on how to keep the conversation going. Here are some tips:

  • Be prepared

Pick a few questions that feel like your style and have those ready when you’re going out to an event or for that dead time before a Zoom meeting.

  • Be open

After the initial question, try to probe a bit more. If they weren’t particularly expansive in their answer, try asking why. 

You could say, “I’m curious about that because I have a different experience. Why did you go that route?” or “Oh, I’ve never been there. Could you describe a bit more about what it’s like?

  • Be vulnerable

By sharing a bit about yourself, you make it a bit easier for the other person to respond. Think of these as breadcrumbs that encourage conversational flow. This can be particularly helpful when engaging those who tend to be more introverted.   

  • Be engaged

Making eye contact and nodding your head shows that you’re paying attention to what the other person is saying, which tends to make people more comfortable and open to sharing more.

  • Pay attention to the group dynamics

If you’re in a group of people and some haven’t responded to the first few questions, try asking them what they think. This may help them feel included and enter the conversation more seamlessly.
Find 30 Conversation Starters for People You Don’t Like to help navigate those trickier conversations.

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