77 Ice Breaker Questions to Go Deeper - making small talk more meaningful

Lately, it feels like everyone’s talking about how lonely people are these days. With so many ways to connect, it’s weird how disconnected we can feel from the people right in front of us. Maybe that’s why more of us are joining clubs, picking up new hobbies, or scrolling social media. Honestly, I don’t think it’s that people aren’t interested in deeper conversations. Most of the time, we just don’t know how to get past the surface-level small talk.

I have a confession for you. Small talk gives me anxiety. It always has. I can go deep quickly but I've never felt comfortable mining the surface for a small nugget of gold.

I watched a reel earlier this week, and I wish I saved it - so I could give you specifics today as I sit and type. It went kind of like this:

A neurotypical guy goes on a date with an Autistic woman, and he is asking her a bunch of typical questions about herself - when she finishes answering she says "Now can I ask you a question?". He says yes, and she says...

"Tell me every detail you remember about your 18th birthday."

He was taken back because he was trying to stay superficial, and she was trying to know who he was as a person.

I LOVED this. This approach does a few of things: 1. It shows you are unique, and trying to get to know the other person. 2. It gets them talking about themselves on a deeper, non-threatening kind of way. 3. I think it will take them more than 10 seconds to answer this question. 4. It gives you the ability to ask more questions about them.

This approach is asking for disclosure and authenticity. This builds trust and connection.

So, in the spirit of connection....here's 77 ice breaker questions. Pick one or two to try at your next social event.

1. Obviously... Tell me everything you remember about your (18th) (whatever) birthday.

Work-related Questions

1. What do you enjoy most about your current job or role?

2. If you could change one thing about your work environment, what would it be?

3. What initially attracted you to your current career path?

4. How do you stay motivated during challenging projects?

5. What’s the most rewarding part of what you do?

6. What skills have you learned at work that you never expected to use?

7. How do you balance your professional goals with your personal life?

8. What does success mean to you in your career?

9. Have you ever had a mentor or someone who influenced your career decisions?

10. If you could start a business, what kind of business would it be?

11. How do you approach problem-solving in your work?

12. What’s the best piece of advice you’ve received in your professional life?

13. What’s one project you’re particularly proud of?

14. How do you usually handle work-related stress?

15. What’s one thing you wish people understood about your job or industry?

Questions for New Friends

1. Tell me everything you remember about your (18) (21) birthday

2. What’s something you’re really passionate about outside of work?

3. If you had a free weekend with no plans, how would you spend it?

4. Do you have a favorite memory from childhood that you think about often?

5. What’s the last thing you learned about yourself?

6. Do you have a favorite hobby or activity you always look forward to?

7. What’s the most interesting place you’ve ever visited?

8. If you could try any new skill or activity, what would it be?

9. What kind of music, movies, or books do you enjoy the most?

10. If you could live anywhere in the world, where would it be and why?

11. What does your perfect day look like?

12. Who inspires you the most in your life?

13. Is there a goal or dream you’re currently working toward?

14. What’s something you recently experienced that made you happy?

15. How do you usually spend time when you’re with friends?

16. If you could instantly master any talent or skill, what would it be?

Questions for Close Friends

1. What’s something you’ve always wanted to do but haven’t yet?

2. What’s the biggest lesson life has taught you so far?

3. How do you typically recharge when you’re feeling burnt out?

4. What’s one of your favorite memories we’ve shared together?

5. If you could relive one moment in your life, what would it be?

6. What’s a quality you value most in the people you surround yourself with?

7. How have you changed the most in the past five years?

8. What’s a topic or issue you’ve been thinking a lot about recently?

9. If you could describe your ideal life in five years, what would it look like?

10. What’s a challenge you’ve faced recently, and how did you overcome it?

11. What’s one thing you appreciate about our friendship?

12. How do you approach making tough decisions in your life?

13. Is there something you’ve been meaning to share but haven’t yet?

14. What’s a personal value or principle that’s really important to you?

15. If you could change one thing about how you spend your time, what would it be?

Questions for Family

1. What’s one thing about our family history you think is important to know?

2. What’s a memory from your childhood that stands out the most?

3. What’s something you’re really proud of in your life?

4. If you could share one piece of advice with the next generation of our family, what would it be?

5. What’s one tradition in our family that you hope will continue?

6. How do you think our family has shaped who you are today?

7. What’s something about our family that makes you smile?

8. What’s a lesson you’ve learned from one of our family members?

9. If you could spend one whole day doing something you love, what would it be?

10. Is there a goal or dream you’ve always had but haven’t pursued yet?

11. What’s the best piece of advice you’ve ever received from a family member?

12. What’s one thing you’ve learned from your experiences that you think others could benefit from?

13. If you could change anything about the way we connect as a family, what would it be?

14. What do you appreciate most about our family?

15. Is there a story about our family’s past that you think more people should know?

Questions for a First Date

1. What’s something you’re really passionate about?

2. Do you have a favorite way to spend your weekends?

3. What’s a trip or vacation you’ve always wanted to take?

4. If you could have dinner with any historical figure, who would it be and why?

5. What’s something about yourself that most people don’t know?

6. What’s your favorite way to unwind after a long day?

7. If you could live in any city or country, where would it be?

8. What’s your go-to comfort food or favorite dish to cook?

9. What’s one experience or event that’s been really meaningful to you?

10. How do you usually celebrate your birthday?

11. What’s a random fun fact about you that you love to share?

12. If you could learn any new skill instantly, what would you choose?

13. What kind of things make you laugh the most?

14. Is there something you’ve always wanted to try but haven’t yet?

15. What’s something small that instantly makes your day better?