100 More Ice-Breaker Questions for Any Group Gathering

Each week in our newsletter we include one question you can use as an ice-breaker for conversations with colleagues at the beginning of meetings, or to post on your internal workplace messaging platform. Some serious, some silly, but all with the intention of leading to further conversations and building community. Last year at this time, with so many of us preparing for a season of holiday gatherings, we compiled 100 of these questions together in one place. Below are 100 more; questions we originally posted back in 2022 and 2023. While some are work-related, the majority of them would work perfectly in any gathering of people. These questions are available as a PDF also; If you’re gathering with others this week, feel free to print these out, cut them up on strips of paper, and have people pick one out of a hat to answer:

• What’s something you’re looking forward to in the upcoming year?
• What’s something you enjoy about a snowstorm?
• When’s the last time you were outside at sunrise?
• What’s something you can do well that you taught yourself how to do?
• Tell us about a mentor you’ve had, and what you’ve learned from them.
• What skill have you worked the hardest to improve over the last five years? How have you done it?
• What’s a skill someone volunteered their time to help you learn?
• What’s the last thing you spent money on?
• What’s the last novel you read (or listened to)?
• Who has been an inspiration to you recently?
• Who’s the last person you said “Thank you” to? What for?
• What’s something in recent memory that has influenced you to think differently?
• Would you rather win an Emmy, a Grammy, an Oscar, or a Tony?
• Who would you say has been a mentor for you in recent years? Would they see themselves as your mentor?
• Who has been a mentee for you in recent years? How has that relationship changed you?
• What’s your wake-me-up drink of choice? How do you like it?
• What’s ‘one cool thing’ that you’re enjoying at the moment?
• What’s a TV show you enjoyed watching when you were a child?
• What was a favorite movie of yours when you were a child?
• What animal do you connect with the most?
• Who’s a fictional character you identify with?
• If you could spend a year in any continent, which continent would you choose?
• What’s a favorite Summer activity of yours?
• What groups are you a part of that support you, your passions, and your interests?
• What’s your favorite summer blockbuster movie?
• How tidy or messy was your bedroom as a child? Is it the same now that you’re an adult?
• If you had the rest of the day entirely free for you to spend how you choose, what would you do?
• What’s something you learned about work from your family members growing up?
• What’s your favorite drink (that’s suitable to drink in the workplace)?
• What kind of fiction do you enjoy the most?
• What’s a work habit you have that others on your team don’t know about?
• If you could pick the perfect time to go to bed – to the minute – what time would that be?
• What’s a magazine you read on a regular basis, or the first one you remember reading as a child?
• What’s the furthest place you’ve ever been from where you are right now?
• If you had the choice of ordering any food for take-out/delivery, what dish would you order, and from where?
• Do you have a favorite series of books? What do you like about it?
• Tell us about a wedding you remember.
• What was your first job? What did you learn from it?
• What movies can you recite the opening lines from?
• If you could play one musical instrument every day of your life – just for fun without ever playing it particularly well – which instrument would you want to play?
• If you could change the color of the sky and the clouds to any other color for the next week, what colors would you choose and why?
• Which of your senses are the most acute?
• Is your personality more like that of a cat, a dog, or some other animal?
• If you have a dollar – just a dollar – to spend on a personal treat for yourself, what would you spend it on?
• Where in your life or your work are you currently pursuing comfort when what’s called for is a little discomfort?
• In which areas of life are you still holding back until you know what you’re doing?
• How would you spend your days differently if you didn’t care so much about seeing your actions reach fruition?
• What was a gift someone gave you years ago that you remember fondly?
• What’s a gift you gave to someone else that you’re proud of, or really liked?
• What’s the nicest thing someone’s done for you recently?
• Describe an experience you’ve had of being lost, and how the situation resolved.
• Describe a favorite movie character of yours. What character traits make them a favorite? Do you share those character traits?
• What’s been a highlight of your day so far?
• What are you looking forward to most in the rest of your day?
• What was the last thing you bought for $2.00 or less?
• What’s something you like about the town (or village/city) you live in?
• What’s something you wish was different about the world?
• What’s your favorite time of the week?
• If you had to pick a time to the exact minute, what’s your favorite time of day?
• What’s something you’ve learned in the last 24 hours? It could be a fact or a reflection, big or small.
• Do you have a favorite place to go for tea or coffee? If so, where? What do you like about it?
• What’s a real-life location from a TV show or movie that you’d like to visit in person?
• What family stories have you heard from the 1960s?
• If you could perform (or conduct) any piece of music perfectly for an audience, what piece of music would you choose?
• What was the last thing you planted in soil (if anything)? How did it grow?
• Does it affect your enjoyment of a story if you know how it ends?
• Finish this sentence: I know from experience that…
• When was the last time you were on a boat of any kind?
• What’s the best thing you’ve eaten recently?
• What’s the worst food you’ve eaten recently?
• If you could only eat one fruit (and all non-fruit food) for the rest of your life, which fruit would you choose, and why?
• If you could visit one landmark anywhere in the world tomorrow (without travel hassles etc.) which landmark would you visit?
• What’s the last TV show you started watching and gave up on? What led you to stop watching?
• What is your favorite sequel of any kind (movie, book, etc. – however you want to answer)?
• What was your favorite thing about yesterday?
• What’s something you’ve done recently outside of work that you’re proud of?
• What’s a project you’re currently engaged in outside of work?
• What’s an ice breaker activity that you have enjoyed doing?
• If you were to choose a puzzle to do, how many pieces would you want the puzzle to have? Are you a 1,000 piece puzzler? A 24 piece puzzler? A 250 piece puzzler?
• If you could choose a board game for us to play right now, what would you choose?
• What’s an app you use a lot that others might enjoy?
• What’s the furthest you’ve ever been from where we are right now?
• What’s the last thing you bought that changed your life?
• How does the new academic year affect your daily schedule?
• If you had to live in any fictional world from movies, books, or other media, which world would you choose, and why?
• What’s a bucket list item that you’ve already done?
• What’s something you’ve been proud of recently?
• What was your first ever work experience?
• Do you remember ever having an exam or test that you aced? Or one that you flunked?
• Imagine you have $17 to spend today and if you don’t spend it you’ll lose it. What would you spend it on?
• What’s a way you often show your appreciation for someone?
• What’s the first album you remember choosing to listen to in full? Have you listened to it recently?
• What’s the most surprising animal you’ve ever seen in the wild?
• If you had to hide a giraffe to keep it safe, where would you hide it?
• What’s your go-to dish to bring to a potluck?
• Who was the first person you spoke to today (apart from those you live with)?
• What’s your favorite present you’ve received in recent years?
• What’s a question you’ve found yourself asking a lot this year?

If you use these this week, we’d love to hear from you to hear how it goes.

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