Not Another Icebreaker: 75 Questions That Actually Spark Connection

For a long time, I thought being a good conversationalist meant always knowing the right thing to say. Usually, that looked like trying to relate to people with my own, similar anecdotes or attempting to give advice. But the older I get, the more I realize that greater connection comes from talking less. Instead of compulsively filling silence, I’ve learned that asking deeper questions creates space for someone else to be seen.

In the past year, I’ve moved to a new city and met dozens of new people. When I realized I was accumulating acquaintances rather than really forging relationships, I started to evaluate my conversations. While they were lively and entertaining (for the most part—you can’t click with everyone), I realized we bounded around from topic to topic rather than ever going deeper. To address that, I’ve noticed that asking thoughtful, open-ended questions can turn small talk into something more meaningful. And often, it just takes one good question to open the door.

So, if you’ve ever wanted to feel closer to someone—at work, amongst acquaintances, during a weekend getaway with friends—this list is for you. These 75 icebreaker questions are meant to help spark genuine connection in every kind of setting.

Feature image from our Desert Dinner Party with Wonder Valley Founder, Alison Carroll.

Using Questions to Create a Deeper Connection

Everyone is talking about the loneliness epidemic. It feels like, despite more opportunities to connect than ever, we’re more disconnected from the people around us. It’s why so many of us are joining clubs, finding hobbies, or trading social media for Substack. In my experience, it’s not that people don’t want to go beyond polite small talk. It’s just that so many of us don’t know how.

But whether it’s making time for water cooler talk at work or asking your friends how they’re really doing, asking the right questions can go a long way. From deep, personal questions to fun thought experiments, here are 75 questions that can deepen your relationships.

At Work

What are you most looking forward to this week? What’s your favorite thing to do on the weekend? What are you most passionate about at work? Did you ever think about trying a different career before this one? What were you like in school? What makes you feel fulfilled? What is your favorite way to unwind? What are some words you live by? What’s the biggest risk you’ve ever taken? What’s something valuable you’ve learned during your career? What’s one thing you’re most proud of accomplishing? If you could have any talent, what would you choose? If you had to be a character from a book, who would you be? If you could live anywhere, where would you go? When do you feel the most yourself?

With New Friends

What is your latest guilty pleasure? Where is the most beautiful place you’ve ever traveled? Tell me about a formative “core memory.” What’s one thing you’re obsessed with right now? Who inspires you? Where is your dream vacation? Have you read/seen anything recently that changed your perspective on something? Do you have siblings? If so, what were you like as kids? What decisions did you make in your early twenties that shaped who you are? What’s the best live show/concert you’ve been to? What’s something you think about all the time? What does your best self look like? What is something you wouldn’t trade for all the money in the world? What’s your favorite thing about this city? What’s your least favorite? What’s the best piece of advice someone has ever given you?

With Family

If you could only listen to one song for the rest of your life, what would it be? What character from a TV show/movie reminds you of me? If you could have dinner with anyone, who would it be? What is your wildest, most impractical dream? What’s your favorite season, and what does it remind you of? What’s your favorite holiday? Describe your perfect day in meals—breakfast, lunch, and dinner. What have you learned recently that you can’t stop thinking about? What is something you want to learn? What’s missing in your life right now? What is the number one item on your bucket list? What/who do you wish you had more time for? What’s one habit you want to make and one you want to break? What are you most excited about? In one year, who do you want to be? In five? Ten?

For Significant Others

Do you have a favorite childhood memory? What assumption do people make about you? What’s one thing you’re trying to work on right now? What’s one thing you’re really proud of? What was your dream job as a child? What does a day in your dream life look like? What does our relationship reveal to you about yourself? What’s the last thing that made you cry? How have you changed since you were a kid? What would you like people to remember you for? Have any of your beliefs evolved over time? How did your childhood shape who you are? What’s one thing you’re passionate about? What would you say to your younger self? What’s the most meaningful relationship you’ve ever had?

With Close Friends

What have you been thinking about recently? What did you think about [insert recent show, movie, book]? Have you read anything interesting lately? What have you been meaning to make time for? Do you feel like you’re in a planting season or a blooming season right now? When have you felt most loved recently? How do you think you’ve changed since this time last year? Tell me about the memory associated with a photo on your phone’s suggested photos. What do you need right now, emotionally, that you’re not getting? What’s the best thing you have ever added to your routine? When was the last time you laughed so hard your stomach hurt? If you could be anywhere right now, where would you be? What would you do with an extra day of the week? Where are you getting your energy from these days? How can I show up better for you right now?