75 Icebreaker Questions For Deeper Relationships

For a long time I thought being a good conversationist meant knowing what to say at all times. Usually it seemed to relate to or try to give advice to someone who had similar anecdotes of themselves. But the older I get, the more I realize that greater connections come from speaking. Instead of forcing silence to fill, I have learned that asking deeper questions creates spaces for someone else to see.

Over the past year, I have moved to a new city and met dozens of new people. I began to appreciate my conversations when I realized I was accumulating acquaintances rather than building relationships. They were lively and interesting (mostly you can’t click with everyone), but I realized that instead of getting deeper than ever before, they put a boundary from topic to topic. To address this, I realized that by asking thoughtful and free questions, I could turn small stories into something more meaningful. And often, one good question is needed to open the door.

So, if you’ve ever wanted to get close to someone, then on work, during acquaintances, or on weekend vacations with friends, this list is for you. These 75 icebreaker questions are intended to help inspire authentic connections in all kinds of settings.

Special image of a dessert dinner party with Wonder Valley founder Allison Carroll.

Use the question to create a deeper connection

Everyone is talking about the epidemic of loneliness. Despite the more opportunities we have connected than ever before, we feel more disconnected from the people around us. That’s why so many of us join clubs, find hobbies, and trade social media for Substack. My experience is not that people don’t want to go beyond polite little stories. That means that many of us don’t know how.

But whether it makes time for a water cooler talk at work or ask your friends how they are Really Doing it and 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 relationship.

At work

1. What are you looking forward to most this week?
2. What do you like on weekends?
3. Do you have the most passion for your work?
4. Have you ever thought about trying another career before this?
5. What did you like at school?
6. What makes you feel fulfilled?
7. What is your favorite way to relax?
8. What are some of the words you live in?
9. What is the biggest risk you’ve ever done?
10. What are the valuable things you learned in your career?
11. What are you most proud of what you have accomplished?
12. If you have talent, what would you choose?
13. If you had to be a character in the book, who would you be?
14. If you could live anywhere, where would you go?
15. When do you feel the most about yourself?

With new friends

1. What’s your latest guilt?
2. What is the most beautiful place you’ve ever traveled?
3. Please tell me about the formative “core memory”.
4. What is one of the things you are working on right now?
5. Who inspires you?
6. Where is your dream vacation?
7. Have you read or watched something recently that changed your perspective on something?
8. Do you have any siblings? If so, what did you like like a child?
9. Did you make a decision in your early 20s that shaped who you are?
10. What is the best live shows/concerts you’ve been to?
11. What do you always think about?
12. What does your best self look like?
13. What are you not going to exchange for all the money in the world?
14. What is your favorite thing about this city? What is your favorite thing?
15. What is the best advice someone has given you?

With family

1. If you can listen to one song for the rest of your life, what would it be?
2. Which characters in the TV show/movie remind you of me?
3. If you could have dinner with someone, who would it be?
4. What is your wildest and most impractical dream?
5. What is your favorite season and what does it remind you?
6. What is your favourite holiday?
7. Describe the perfect day of meals – break first, lunch, dinner.
8. Have you recently learned that you can’t stop thinking?
9. What do you want to learn?
10. What is missing in your life?
11. What is the best item on your bucket list?
12. What/Who would you like to spend more time?
13. What habits do you want to make and what you want to break?
14. What’s the most exciting?
15. Who do you want to be in a year? In 5? 10?

For important others

1. Do you have any favorite childhood memories?
2. What assumptions do people make about you?
3. What is one thing you are about to tackle right now?
4. What are you really proud of?
5. What was your child’s dream job?
6. What does your dream life look like?
7. What does our relationship reveal to you about yourself?
8. What was the last thing that made you cry?
9. How have you changed since you were a child?
10. Do you want people to remember you?
11. Has any of your beliefs evolved over time?
12. How did your childhood form you?
13. What are you passionate about?
14. What do you say to your younger self?
15. What is the most meaningful relationship you’ve ever had?

With close friends

1. What have you been thinking lately?
2. What did you think about? [insert recent show, movie, book]?
3. Have you read anything interesting recently?
4. What did you mean to make time?
5. Do you feel like you are now planting season or blooming season?
6. When did you feel most loved recently?
7. How do you think you’ve changed since last year?
8. Please tell me about the memory associated with the photo of the proposed photo on your mobile phone.
9. Emotionally, what do you need now that you’re not getting?
10. What’s the best thing you’ve ever added to your routine?
11. When was your stomach hurting the last time you laughed?
12. If you could be anywhere now, where would you be?
13. What do you do with the extra days of the week?
14. Where have you gained energy recently?
15. How can you show up better for you now?