336 Icebreaker Questions for Work + Free AI Generator

Need icebreaker questions for work? Check these 336 fun icebreakers to warm up before meetings and boost team connection. Plus, a free AI generator.

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What's the most adventurous thing you've ever done?


Welcome to our ultimate list of icebreaker questions for work to kick off team meetings, workshops, and team-building activities.

Running an awesome icebreaker is key to fostering engagement and building connections at work, especially for hybrid remote and remote work teams.

We've collected the best icebreakers for work:

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Still on Zoom or Teams? Online meetings don't have to be dull or annoying. Explore the best virtual meeting platforms to boost your collaboration with fun.

Virtual Icebreaker Questions for Work

These icebreaker questions are perfect for virtual meetings.

They can be answered by people new to the team or team members you’ve known for years.

  1. What's your favorite book or book genre?
  2. Share one interesting fact about your hometown.
  3. Do you have any unique talents or hobbies?
  4. Where would you go if you could travel anywhere in the world right now?
  5. What's your go-to comfort food?
  6. Describe a movie or TV show you've recently enjoyed.
  7. If you had a superpower, what would it be, and why?
  8. Share a memorable childhood vacation experience.
  9. What's your preferred way to relax after a long day?
  10. What's the best piece of advice you've ever received?
  11. 11. If you could have dinner with any historical figure, who would it be, and what would you ask them?
  12. Share a funny or embarrassing travel story.
  13. Describe a skill or hobby you'd love to learn in the future.
  14. What goal are you currently working toward, personally or professionally?
  15. If you could switch lives with a fictional character for a day, who would it be, and what would you do?
  16. Share a memorable adventure or outdoor activity you've experienced.
  17. Discuss a recent act of kindness you witnessed or participated in.
  18. If you were to write a book, what genre would it be, and what would the title be?
  19. What's the most interesting place you've visited and why?
  20. Describe a cultural tradition or festival you enjoy celebrating.
  21. Where and when would you go if you could time-travel to any historical period, past or future?
  22. What's the weirdest food combination you've ever tried and liked?
  23. Share an unusual or unique item on your bucket list.
  24. If you could have a dinner party with three fictional characters, who would you invite, and why?
  25. What's the most adventurous thing you've ever done or an adventure you'd like to embark on?

Funny Icebreaker Question for Hybrid and Remote Teams

Whether you want to shoot straight or make people wish the icebreaker was over, these icebreaker questions go from pretty seriously to seriously funny.

Straight Shooting:

  1. What's your favorite book of all time and why?
  2. Do you have any travel plans for the near future?
  3. What's your go-to comfort food when you need a pick-me-up?
  4. How do you stay motivated in your work or projects?
  5. What's one skill you've always wanted to learn but haven't yet?
  6. Do you enjoy any outdoor activities like hiking or camping?
  7. What's your preferred way to unwind after a long day?
  8. If you could live in any time period, past or future, when would it be?
  9. What's your favorite thing about the city or town you live in?
  10. If you could have dinner with any historical figure, who would it be?

Kinda Funny:

  1. If you could have any superpower, but only for one day, what would it be?
  2. Share a quirky or unusual talent you have, no matter how random.
  3. What's your funniest childhood memory that still makes you laugh?
  4. If you could switch lives with a fictional character for a day, who would it be?
  5. What's the most interesting or bizarre food combination you enjoy?
  6. If you were a professional wrestler, what would your stage name be?
  7. What's the strangest place you've ever fallen asleep?
  8. Share a pun or dad joke that always makes you chuckle.
  9. If your life had a theme song, what would it be, and why?
  10. Describe your dream job, but add a humorous twist to it.


  1. What do you think they'd do if you could swap lives with your pet for a day?
  2. Share a hilarious travel mishap or adventure that you've experienced.
  3. What's the silliest dance move you can do on the spot?
  4. What would it be if you could create a new holiday, and how would we celebrate?
  5. Tell a funny anecdote from a recent family gathering or event.
  6. If you were a stand-up comedian, what would your opening joke be?
  7. Describe the most embarrassing fashion trend you ever followed.
  8. Share a memorable prank you've pulled or been a part of.
  9. What's your go-to karaoke song when you want to make people laugh?
  10. If you could have any animal as a sidekick, which one would it be and why?

OMG, Stop:

  1. If you could have a conversation with a talking animal, what would you ask them?
  2. Describe a wild and fictional adventure you had in a dream once.
  3. If you were a cartoon character, what would your catchphrase be?
  4. Share the most bizarre conspiracy theory you've ever heard of.
  5. What kind of candy would you be if you could live in a candy-themed world?
  6. Invent a wacky new sport and explain the rules.
  7. Describe the plot of a truly outlandish and ridiculous movie you'd love to watch.
  8. What would it be if you could build a house out of any material?
  9. Share a story about a bizarre coincidence that happened in your life.
  10. How would you do it if you had to survive a zombie apocalypse using only items in your room or office right now?

Best Icebreaker Questions for Work Meetings

Whether you’re having a quick meeting and need to break the ice or kicking off a big brainstorming session, these questions are great for meetings.

  1. What would it be if you could have any job in the world for one week?
  2. What skill have you always wanted to learn but haven't had the chance to?
  3. Share a recent book or podcast recommendation.
  4. If you could travel back to any historical event, which would you witness?
  5. What's the most inspiring quote you've ever heard?
  6. Describe a favorite childhood memory.
  7. Share one thing on your bucket list.
  8. What's the best advice you've ever received from a mentor?
  9. If you could have dinner with any living person, who would it be?
  10. What's your favorite way to unwind and relax after a busy day?
  11. Where would you go if you could visit any fictional world from a book or movie?
  12. Share a surprising or little-known fact about yourself.
  13. What's a hidden talent or skill you possess?
  14. Describe a place you've traveled to that left a lasting impression.
  15. If you could instantly be fluent in any language, which would you choose?
  16. What's your favorite way to stay active or fit?
  17. Share a recent achievement or personal milestone.
  18. What advice would you seek if you could converse with your future self?
  19. Describe a hobby or activity you enjoy doing in your free time.
  20. What's a place on your travel wish list you haven't visited yet?
  21. Share a favorite family tradition.
  22. What would it be if you could have any animal as a pet?
  23. What's your all-time favorite movie, and why?
  24. Describe a memorable encounter with a celebrity or public figure.
  25. Share a unique food dish from your culture or heritage.
  26. Who would you be if you could swap lives with someone for a day?
  27. What's the most beautiful natural wonder you've seen in person?
  28. Describe a time when you faced a fear and overcame it.
  29. What's your dream vacation destination?
  30. Share a recent act of kindness you experienced or witnessed.
  31. If you were to start a charity, what cause would it support?
  32. What's the best advice you'd give your younger self?
  33. Describe a challenging problem you've solved at work or in life.
  34. What year would you visit if you could time travel to the future?
  35. Share a memorable childhood TV show or cartoon.
  36. What's the most interesting museum or exhibition you've been to?
  37. What would it be if you could have any type of vehicle (real or fictional)?
  38. Describe a favorite winter activity or holiday tradition.
  39. Share a funny or unique nickname you've had.
  40. If you could witness any historical event, even if you couldn't change it, which would you choose?
  41. What's a quirky habit or superstition you have?
  42. Describe an unusual job or gig you've had in the past.
  43. What would it taste like if you could invent a new flavor of ice cream?
  44. Share a fun fact about your hometown or where you currently live.
  45. If you could meet any fictional character, who would it be, and why?
  46. What's a song that always puts you in a good mood?
  47. Describe a place you'd love to live in for a year without any responsibilities.
  48. What type of cuisine would you request most often if you could have a personal chef?
  49. Share a memorable experience from your school days.
  50. What's a talent or skill you wish you had, even though you know it's unrealistic?

Still on Zoom or Teams?

Get interactive with you remote team in a virtual office. Explore our 5 picks.

Themed Work Icebreaker Questions

Seeking a specific theme? Look no further than the questions below about travel and adventure, pop culture and entertainment, food and culinary preferences, life experiences and aspirations, technology and gadgets, and more.

Travel and Adventure

  1. Where would you choose to go if you could go on a road trip anywhere in the world?
  2. What's the most beautiful place you've ever visited?
  3. Have you ever been on a spontaneous adventure? Share the story.
  4. Where would you pick if you could live in a different country for a year?
  5. What's your dream vacation destination, and why?
  6. Do you prefer the mountains or the beach for a getaway?

Pop Culture and Entertainment

  1. Who's your favorite superhero, and what makes them special?
  2. Who would you be if you could be a character in any movie or TV show?
  3. What's the best concert or live performance you've attended?
  4. If you could meet any celebrity, dead or alive, who would it be and why?
  5. Do you enjoy playing video games? If so, which one is your all-time favorite?
  6. If you could be a contestant on any game show, which one would you choose?

Food and Culinary Preferences

  1. What's your favorite comfort food?
  2. What would it be if you could only eat one cuisine for the rest of your life?
  3. Are you a fan of spicy foods, or do you prefer milder flavors?
  4. What signature dish do you love to cook for friends and family?
  5. Do you enjoy experimenting with new recipes in the kitchen?
  6. Are you a fan of coffee or tea, and how do you take your preferred beverage?

Life Experiences and Aspirations

  1. What's a significant life lesson you've learned recently?
  2. If you could give your younger self one piece of advice, what would it be?
  3. What's a dream or goal you're actively working toward right now?
  4. What would it be if you could make a positive change in the world?
  5. What's the most challenging obstacle you've overcome in your life?
  6. If you could choose a new career path unrelated to your current one, what would it be?

Technology and Gadgets

  1. Do you consider yourself tech-savvy, or do you prefer simpler gadgets?
  2. What's your all-time favorite piece of technology?
  3. If you could invent a futuristic gadget, what would it do?
  4. Are you an early adopter of new tech trends or prefer tried-and-true technology?
  5. What's your most-used app on your smartphone, and why?
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Books and Reading

  1. If you could have a conversation with any author, who would it be?
  2. What's your favorite book genre, and why does it appeal to you?
  3. Are you a fan of physical books, or do you prefer e-readers and digital formats?
  4. What's a book that profoundly impacted your life or perspective?
  5. If you could visit a fictional literary world, which would you choose?

Want to Find a Remote Work Books to Level Up Your Leadership Game?

Check out the top 21 remote work books to create a strong culture and manage teams effectively, from best-selling authors.

Personal Growth and Reflection:

  1. What new skill have you recently learned or want to learn?
  2. How do you typically handle stress and difficult situations?
  3. What's the most memorable advice you've received from a friend?
  4. What would it be if you had to describe your personal philosophy in one sentence?
  5. What's a hobby or interest you'd like to pursue?
  6. How do you define success in your life, personally and professionally?
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Remote Work

  1. Share the most positive aspect of remote work you’ve personally experienced. 
  2. Reveal whether you’ve ever worked in your pajamas, and if so, share a funny or surprising related experience. 
  3. Share your best (or weirdest) home office setup hacks.  
  4. How have you reclaimed the time you used to spend commuting to the office.  
  5. Share your most amusing or awkward experiences during video conferences or virtual meetings. 
  6. If you could have any “remote work superpower” to resolve your most detested remote work challenge instantly, what would it be?

Managing a Remote Team?

Check out our 20 tips for managing remote teams in 2024: Focus on safety, communication, engagement, AI integration, and continuous learning for improved productivity.

Hybrid Work

  1. What would your ideal hybrid workday look like? (Wrong answers only.)
  2. What aspects of commuting do you find most frustrating on office days?
  3. Share your funniest anecdote about remote team members.
  4. What are the must-visit attractions in a world where hybrid work is a theme park?
  5. What would their catchphrase be if hybrid work were a quirky character in a sitcom?
  6. What would be the most challenging event in a parallel universe where hybrid work is a sport?
  7. Imagine hybrid work as a movie plot. Who would lead, and what unexpected plot twist would keep everyone engaged?
  8. If hybrid work were a wildlife documentary, what animals represent different aspects of the experience?"

Icebreaker Questions Based on How Well the Team Knows Each Other

You may be a totally new team. You may know each other for years and babysit each other's kids. No matter what, we have some questions for you to break the ice.

We Don't Know Each Other at All:

  1. If you could have dinner with any historical figure, who would it be and why?
  2. Share one interesting fact about yourself that nobody here would guess.
  3. What's your dream travel destination, and why does it appeal to you?
  4. What job would you choose if you could switch careers for a day?
  5. What's your favorite book or movie, and what do you love about it?
  6. Where would you go first if you could visit any place in the world?
  7. What's a unique hobby or skill you'd like to share?
  8. Describe one thing on your bucket list that you're excited to accomplish.
  9. Share a funny childhood memory or embarrassing moment.
  10. What's the best piece of advice you've ever received.
Check out our getting to know you activities for more ideas.

We've Worked Together for Some Time:

  1. What's one project or achievement at work that you're particularly proud of?
  2. Share a work-related challenge you've faced and how you overcame it.
  3. What's your go-to strategy for managing stress during busy times at work?
  4. What would it be if you could change one thing about our team's dynamics?
  5. What skill have you developed since joining the team that you're proud of?
  6. Describe a mentor or colleague who has significantly impacted your career.
  7. Share a work-related goal you're currently pursuing.
  8. Discuss a recent professional development opportunity that you found valuable.
  9. What's one thing you appreciate most about the team's collaboration style?
  10. If you could offer one piece of advice to a new team member, what would it be?

We Know Each Other Well:

  1. What's one personal goal you're currently striving to achieve outside of work?
  2. Share a memorable team achievement or success story.
  3. What's a valuable lesson you've learned from a past mistake or failure?
  4. Discuss a team member who has inspired you and explain why.
  5. What's one thing you believe our team excels at compared to others?
  6. Share a challenging decision you had to make and the thought process behind it.
  7. What's a hobby or passion project you're currently dedicating time to?
  8. Describe a time when you and a team member successfully resolved a conflict.
  9. What's the best team-building activity or event we've ever had, in your opinion?
  10. Share a short-term and long-term career goal you're actively pursuing.

The Team is Practically Married:

  1. What's one word or phrase that best describes the team's culture and dynamic?
  2. Share a funny or heartwarming team memory that stands out to you.
  3. What's a challenge or obstacle the team faced together and overcame brilliantly?
  4. Discuss a time when the team exceeded expectations or delivered outstanding results.
  5. What's the most important quality you believe every team member possesses?
  6. Share a vision or goal for the team's future that excites you.
  7. Describe a moment when the team's unity and support made a significant impact.
  8. What's a unique team tradition or inside joke that everyone can relate to?
  9. Share when the team went above and beyond for a colleague in need.
  10. What's one thing you deeply appreciate about each member of the team?

Almost Not Safe for Work (Total Bestie Territory) 

  1. If you could travel back to your teenage years, what advice would you give your younger self about love and relationships?
  2. Share a funny or memorable dating experience you've had in your life.
  3. What's the most adventurous or daring thing you've ever done outside of work?
  4. If you could switch lives with a celebrity for a day, who would it be, and what would you do?
  5. Describe a dream or fantasy you've never shared with anyone at work.
  6. What's one thing on your personal bucket list that you're eager to accomplish soon?
  7. Share a unique or unusual hobby or interest that you're passionate about.
  8. If you could have dinner with any fictional character, who would it be, and why?
  9. What's the most romantic gesture you've ever made or received?
  10. Discuss a personal growth journey or transformation you've undergone that has shaped who you are today.

Awkward, Weird Icebreaker Questions:

  1. What would it be if you could only eat one food for the rest of your life?
  2. What's the strangest dream you've ever had?
  3. If you could switch bodies with someone for a day, who would it be?
  4. What's your most unusual talent or skill?
  5. If you had to wear one color for the rest of your life, which color would you choose?
  6. Would you rather have the ability to fly or be invisible?
  7. What's the weirdest fashion trend you've ever tried?
  8. If you could have any animal as a pet, even mythical ones, what would it be?
  9. What's the oddest place you've ever visited?
  10. If you could live in any time period, past or future, when would it be?
  11. What's your favorite bizarre food combination?
  12. Would you rather have a third arm or a third eye?
  13. If you could communicate with any animal species, which would you choose?
  14. What's the most unusual item on your bucket list?
  15. What would it be if you could attend any weird or quirky event in the world?

If You Could Icebreaker Questions:

  1. If you could travel back in time to any historical event, which one would you attend?
  2. If you could meet any historical figure, who would it be and what would you ask them?
  3. If you could have any superpower, what would it be and why?
  4. Where would you go if you could visit any fictional world from a book or movie?
  5. What would it be if you could eliminate one thing from your daily routine?
  6. If you could be a character in any TV show, which one would you choose?
  7. If you could switch lives with anyone for a day, who would it be?
  8. If you could have dinner with any living person, who would it be and why?
  9. Where would you choose if you could live in any country for a year?
  10. If you could change one thing about the world, what would it be?
  11. If you could speak any language fluently, which one would you pick?
  12. What would it be if you could have any job for one week?
  13. If you could instantly master any skill, what would it be?
  14. If you could be a character in any video game, which one would you choose?
  15. If you could time-travel to the future, what year would you visit?

Would You Rather Icebreaker Questions:

  1. Would you rather have the ability to read minds or see the future?
  2. Would you rather have a personal chef or a personal trainer?
  3. Would you rather explore the deep sea or outer space?
  4. Would you rather have unlimited money or unlimited free time?
  5. Would you rather always be 10 minutes late or 20 minutes early?
  6. Would you rather never be able to speak again or always have to speak your mind?
  7. Would you rather have the power of teleportation or the power of invisibility?
  8. Would you rather always have perfect weather or never have to wait in line again?
  9. Would you rather live in a treehouse in the forest or a houseboat on the lake?
  10. Would you rather be a famous actor or a brilliant scientist?
  11. Would you rather never need to sleep or never need to eat?
  12. Would you rather be a wizard in a fantasy world or a space explorer in the future?
  13. Would you rather have the ability to time-travel or stop time temporarily?
  14. Would you rather be a famous musician or a famous athlete?
  15. Would you rather have the power to heal others or the power to control the weather?
If you like these would you rather questions, you'll probably also like our hundreds of would you rather questions and free AI this or that generator!

Holiday and Christmas Icebreaker Questions:

  1. What's your favorite Christmas tradition or activity?
  2. If you could spend Christmas anywhere in the world, where would it be?
  3. What's the best Christmas gift you've ever received?
  4. If you could choose a different holiday to celebrate in December, which would it be?
  5. What's your go-to holiday movie or special?
  6. If you could create a new Christmas tradition, what would it involve?
  7. What's your favorite Christmas cookie or treat?
  8. If you could be in a Christmas movie, which character would you play?
  9. What's the most memorable Christmas decoration you've seen?
  10. What would it be if you could give a gift to everyone in the world?
  11. What's your favorite Christmas song, and can you sing a few lines?
  12. What would it be like if you could design a Christmas-themed amusement park ride?
  13. What's your favorite holiday memory from your childhood?
  14. If you could have a magical Christmas adventure, what would it entail?
  15. What's your wish for the world during the holiday season?
Read work Christmas party ideas, Halloween ideas for work to explore more ideas on engaging with others.

Community Building Questions:

  1. What's one thing you love about the community you live or work in?
  2. If you could organize a community event, what would it be?
  3. What's our community's most important issue, and how can we address it?
  4. If you could improve one thing in our community, which would it be and how?
  5. Who is someone in the community you admire for their contributions?
  6. If you could lead a community project, what would its focus be?
  7. What's the best community event you've ever attended, and what made it special?
  8. What positive impact would it have if you could organize a community event?
  9. What's a hidden gem in our community that more people know about?
  10. What's your vision for a more inclusive and connected community?
  11. If you could organize a fundraiser for a charity, which one would you choose?
  12. What's the most memorable act of kindness you've witnessed in our community?

Find Your Best Virtual Meeting Platform

Check out our comparison guide of the most effective and engaging Virtual Meeting Platforms to find your best options.

How to run a great icebreaker at work

With over 300 icebreaker questions for work, you should have enough to choose one that fits you.

But how to run an icebreaker successfully? Here are some tips to help you make your icebreakers successful:

Set the right tone

At FlexOS, we always believed that an icebreaker is essential to kick off a good day. By engaging in fun activities and asking related questions before any team discussion or meeting, we create a comfortable environment and mutual understanding.

To start with, it's important to inform everyone about the icebreaker and get them ready for it.

Some activities require prior preparation, while others can start right away.

However, it's crucial to ensure that everyone is aware of what we're doing and on board. Even the most entertaining game won't be enjoyable if the group isn't  actually playing.

Choose appropriate questions

Tailor your icebreaker questions to fit the context and the familiarity level of your group. Use a traffic light framework, starting with easy questions for new or less familiar groups and gradually escalating to deeper, more personal questions for closer-knit teams.

Traffic Light for Icebreakers

Experiment with different icebreaker formats to keep things fresh and engaging. Sequential answers work well for smaller groups (split them with this Random Group Generator), where each participant takes turns sharing.

For larger groups, consider using a format like "Never Have I Ever" that allows everyone to participate simultaneously.

Keep it short and fun

Usually, an icebreaker should be over within 15-20 minutes, unless you're having a separate session specifically for building connections and engagement. Just make sure to plan for some extra time for the icebreaker, so you don't go over the meeting time and annoy everyone.

For daily meetups, icebreaker questions are the go-to option for any team. FlexOS AI Icebreaker Generator provides unlimited icebreaker questions that are tailored to your purposes to help foster team engagement and create a positive setting for upcoming productive conversations.

For more tips on running engaging session, check out our tips on meeting facilitation and our favorite book The Art of Gathering.

Final Thoughts

When planning an icebreaker activity, it's important to remember that its purpose is to help your team feel comfortable and prepared to work together.

Don't worry too much about crafting the perfect icebreaker - as long as you're genuinely trying to make the hybrid and remote work experience more engaging for everyone involved, you're on the right track.

Try icebreaker questions with your team using FlexOS AI Icebreaker Generator tool now! 👆

To keep the momentum going, we recommend checking out our guide on choosing the right virtual meeting platforms to organize a successful virtual meetings or choose one of these five great virtual workspaces.

As a manager, you have the power to transform the remote working experience by prioritizing a positive and aligned team culture. Take a look at our guide to ace managing remote teams to get started today.

FAQ about Icebreaker Questions for Work

What are icebreaker questions?

Icebreaker questions are prompts during meetings or activities to facilitate introductions and foster participant connections.

These questions can range from fun and silly to serious or quirky and aim to reveal something personal about the people answering them, such as their favorite food or movie.

It helps to connect people and keep teams in sync.

What makes the best icebreakers effective?

The best icebreakers reveal minor aspects of personality and prompt fun and memorable answers.

For instance, asking about someone's favorite paint color or college experiences can lead to engaging conversations.

Unique and quirky questions often work well, adding an element of intrigue to the icebreaker.

How do you successfully ask icebreakers questions for work? 

Running icebreakers successfully involves starting with simple, fun questions that allow quick responses.

Establishing the order in which participants will answer the questions is essential to create a smooth flow.

As the group becomes more comfortable, you can gradually increase the complexity of the questions to keep things interesting.

Should you ask funny questions during icebreakers?

Skip the awkwardness!

The appropriateness of funny icebreaker questions depends on the setting and tone of the meeting. Fun or silly questions can boost spirits in a work meeting but may not be suitable right before announcing a layoff.

Consider using interesting and unique questions to keep the icebreaker engaging when in doubt about the tone.

How to facilitate an icebreaker effectively? 

Facilitating an icebreaker involves three key steps:

  • Kicking it off: Choose someone to go first, which can be you if it's a new team, helping set the tone for participation.
    If the group is too big, use the Random Group Generator.
  • Making sure everyone participates: Ensure that every participant has a chance to answer the icebreaker question to foster inclusivity.
  • Wrapping it up: When all participants have shared their answers, conclude the activity and thank everyone for participating.

How can icebreakers be used beyond introductions? 

Icebreakers can serve multiple purposes beyond introductions, such as getting to know your team members, understanding their perspectives and experiences, building community at work, and more. 

When is the best time to use icebreakers during meetings? 

Icebreakers can be used early in a meeting to establish a sense of community and break the ice.

They can also be incorporated throughout meetings to maintain engagement and build participant connections.

The timing and frequency depend on your specific goals and needs.

What can I do beyond icebreakers?

As we work more distributed than ever, you may wonder how to engage remote employees.

I suggest employing employee engagement strategies to keep your team working well together regardless of location.

Practice employee engagement best practices and use employee management software or employee engagement tools to excel.

To truly excel in employee engagement, consider working with employee engagement survey providers.

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