the art of asking

on the beauty of deep conversations and a personal archive of questions

there’s nothing i love more than asking questions. diving into deep conversations, feeling like nothing in the world exists but us.

i think i fall in love a little with every person i meet. i crave to know the experiences, the intricacies, the stories of how people came to be who they are. i say this because i genuinely find beauty in everyone. not necessarily in a romantic sense, but in that soul-level kind of admiration. the kind that exudes from how someone tells a story, the pauses in their voice, the sparkle in their eyes when they talk about something they love. it’s in the way their words unknowingly reveal their own processes of becoming.

there’s nothing quite like the art of deep conversations. opening ourselves up to questions that feed our souls, that connect us in a way few other things can. the kinds of questions that make time blur and remind us how human we are.

over the past three years, i’ve collected a series of questions in my notes app, titled personal connections. in moments when i long for depth in a conversation with a friend or loved one, i pull it out, almost like carrying a pocket-sized we’re not really strangers with me everywhere i go.

i take pride in it because these questions didn’t come from just anywhere. they’ve been curated through different forms of media, borrowed from late-night talks with people i love, or even from my own thoughts when i’m alone with myself. it’s a growing archive of curiosity and of care! and for my very first substack article, i want to share some of my favorite ones with you:

1. what’s a topic you could talk about for hours?

2. would you be friends with yourself?

3. what are small things that aren’t so small to you?

4. would your younger self be proud of yourself now?

5. what are your strengths as a friend?

6. what makes you want to be a better person?

7. what’s your favorite childhood memory?

8. what’s a hard pill of yours to swallow at the moment?

9. when do you feel the most appreciated and valued?

10. what is something you’ve been actively pursuing?

11. how do you best connect with others?

12. what keeps you alive nowadays?

13. what is your idea of a perfect weekend?

14. what remains unchanged about you since your childhood?

15. if someone offered you a box containing everything you ever lost, what would you look for first?

16. how long is the longest you’ve had feelings for someone?

17. how do you show love?

18. do you think there’s a part of you that you’ve lost?

19. what’s something you wish you could experience or feel for the first time again?

20. what’s your favorite thing about yourself?

as much as i appreciate small talk, nothing quite compares to questions like these. a single one can unfold into an hour of conversation. it’s layered, open-ended, and always evolving. it’s as if each question holds a map to someone’s inner world, and all we have to do is ask.

how beautiful is it that questions are the windows to one’s mind, one’s heart?

i hope this list serves as an invitation; not just to ask more questions, but to listen in a deeper level. to pause. to connect. whether it’s with a friend, a partner, a stranger, or even with yourself. because sometimes, all it takes is one question to remind us that we’re not so alone in what we’re feeling. that we’re all still becoming. that we’re all still trying to be seen.

this will remain my favorite way to fall in love with the world again and again—with a question, and the heart that answers it :)