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36 Questions That Lead To Empathy

Let’s talk about what isn’t on your highlight reel.


As my final year of college draws to a close and I reflect on these past four years, what sticks out most is the strength of the relationships I’ve built with some incredible people I’m so fortunate to have met.

I admit that the anonymity of a university overflowing with 29,000+ undergraduates got to my head at times. Meeting new people was easy, sure, but since it was impossible to get to know them all intimately, I gleaned what I could from the likes of Facebook and Twitter.

Glowing photos from study abroad, acceptances of job offers from Google, wedding proposals. Popular, successful, happy. Everyone living their best life. I quickly learned that the “connectedness” promised by social media actually leaves us emptier and lonelier than ever.

The time I spent in person with my closest communities became my therapy. It was during lunches at Mezzo, walks by the Marina, and drives up to Lawrence National Laboratory, over moments of real human connection and physical time spent together, that I found comfort, validation, and belonging in exchanging insecurities, anxieties, and failures.

We could all do more to encourage a culture of sharing the imperfect moments and thoughts that make us human — the ones that don’t necessarily see the light of Instagram, Facebook, and LinkedIn feeds, or even group dinners and parties.

Inspired by the viral 36 questions that lead to love published by New York Times a couple of years ago, here are 36 questions to dig a little deeper with those in your life and let them know you care.

The only rule? Grab someone and exchange answers in person.

Don’t give advice. Just share, listen, and be there for each other because vulnerability and compassion go a long way in a decade that feels severely deficient of empathy.


36 Questions That Lead To Empathy

Set 1: Self

1.What do people admire about you the most? What do you want to be admired for?

2. Share the details of a day you felt overwhelmed.

3. What’s a go-to comfort food or restaurant?

4. When’s the last time you paid for something that wasn’t worth it?

5. What’s your creative outlet?

6. When was the last time you cried alone? When was the last time you cried in front of someone else?

7. Share a time you were handed something you felt you didn’t deserve.

8. Share a time you felt left out.

9. Do you have any songs that make everything okay when you listen to them?

10. When was the last time you were really disappointed?

11. Sunrises or sunsets?

12. If you could make one change to your body, what would it be?

13. When was the last time you received a rejection (of any kind)?

14. Share something about yourself that you’ve never told anyone before.

Set 2: Others

15. Share a time a stranger did a nice thing for you. What about a time you did a nice thing for a stranger?

16. When was the last time you made up an excuse to not come to a social event? What was the excuse?

17. Share a time you lied to protect someone.

18. Who’s the first person you tell about the big moments in your life?

19. Who’s the last person that broke your heart? What helped you move on?

20. If you could go back and apologize to one person, who would it be and why?

21. How often do you meet up with your friends?

22. What’s the most jealous you’ve ever been of someone?

23. What’s your relationship like with your parents? With your siblings?

24. When was the last time you fought with someone close to you? What was it about?

25. Have you ever taken advantage of someone intentionally?

26. When was the last time you broke a promise you made to someone?

27. Who is someone in your life you look up to? What are they like?

Set 3: Meaning/ Purpose

28. What’s going well and what’s not going so well in life right now?

29. How far into your future have you thought about?

30. What’s your biggest fear?

31. If you want kids, what kind of parent do you want to be? If not, how come?

32. What do you need to feel happy and fulfilled?

33. What does failure look like or mean to you?

34. Do you believe in fate? Explain.

35. Are you scared of death? Why or why not?

36. What made you most excited to get out of bed this morning?

Optional: Hug each other and pass these on.

Originally published at medium.com

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