These questions are designed to spark conversation, laughter, and connection—whether you’re meeting for the first time or want to deepen bonds within your group.
Fun & Lighthearted
- If you could have any superpower, what would it be and why?
- What’s your go-to karaoke song?
- If you could travel anywhere in the world right now, where would you go?
- What’s the last TV show you binge-watched?
- If you could only eat one food for the rest of your life, what would it be?
- What’s your favorite way to spend a day off?
- Do you have a hidden talent? What is it?
- What’s your favorite movie of all time?
- If you could swap lives with any fictional character, who would it be?
- What’s the weirdest food you’ve ever tried?
Thought-Provoking
- What’s something on your bucket list you haven’t done yet?
- If you could meet anyone—living or dead—who would it be?
- What’s the best piece of advice you’ve ever received?
- What’s a skill you wish you had?
- What’s one thing you’re grateful for today?
- If you could instantly master any language, which one would you choose?
- What’s a book that changed your perspective?
- What’s your favorite way to relax and unwind?
- What’s the most adventurous thing you’ve ever done?
- If you could time travel, would you go to the past or the future?
Getting to Know You
- What’s your favorite childhood memory?
- What’s your favorite holiday tradition?
- If you had a theme song that played whenever you entered a room, what would it be?
- What’s your favorite thing about where you grew up?
- What’s your favorite season of the year, and why?
- Do you prefer mornings or nights?
- What’s your favorite hobby or pastime?
- What’s a fun fact most people don’t know about you?
- What’s your favorite family recipe or dish?
- What’s something you’re looking forward to this year?
Tip: Choose a few questions to start, or let group members pick their favorites. You’ll be surprised at how quickly these questions can break the ice and spark meaningful conversations!
Feel free to use and share this list at your next gathering!
Catherine Fitzgerald is the founder and Chief Executive Officer of Oak Innovation. With 30+ years of experience in the training and development industry, Catherine and her team at Oak Innovation are ideally positioned to help training professionals, business managers, and entrepreneurs access customizable training course material.
