I found this old note with a list of questions I was playing with in conversations.
Using pre-written questions is something I rarely do anymore, because I find that the best questions arise from whatever it is that the other person evokes a desire in us to know the answer to .
But I remember these giving me a lot of mileage.
Back when I was going out daily to do social exploriments, I’d occasionally have moments when I seemed to blank out or lose touch with my ability to flow.
For example, after a string of awkward interactions, I’d suddenly struggle to take any conversation further than just an introduction. Or I’d be at a big event where I didn’t know anyone, and I’d forget how to start a conversation.
In such moments, I found it really helpful to have 1 or 2 go-to questions for each situations that would get me unstuck, something to fall back on.
Enjoy playing with these!
Unusual Conversation Starters
In my teens and twenties, I spent a lot of time approaching strangers on the street (I’m still friends with some of them, though they’re no longer strangers).
Initially, the hardest part seemed getting over the fear of doing so. But once that got easy, what I turned out to find the hardest was keeping the conversation interesting.
These questions all came from the idea that I could solve this by simply starting a conversation with a question that prompts an interesting dynamic:
- What’s your go-to line for talking to strangers? (/making conversation with someone you don’t know very well?)
- Do you like small talk or prefer to skip it? Why?
- Any advice for someone trying to get better at starting conversations?
- What are you excited about lately?
- Have we talked yet? What do you LOVE talking about? (/ what do you wish more people asked you about?)
- Be honest, what were you thinking about just now?
- What was the highlight of your day so far?
- Why do you think it’s often so weird / scary to walk up to someone new?
Wild cards:
- …Did you feel that? / Are you feeling it?
- …Now what?
- What’s one thing that could make this day even better?
(these 2 can lead to very interesting conversations if there was already a connection before you spoke, but if there was any sense of disconnect or awkwardness, they will amplify it)
Questions to Transition from Small Talk to Personal Conversation
I wrote a more in depth article on how to move between the 6 Levels of Conversational Depth here.
The questions below can mostly be used in response to small talk (level 1) to more personal conversation (level 2 or 3).
- What do you love most about [job / hometown /hobby]?
- How did you end up in [job / hometown /hobby], and had you expected it?
- How has [ job/culture/hobby ] shaped the way you see the world?
- Any advice for how to transition from small talk to deeper conversation?
- What does a typical day in your life look like?
- What makes you laugh more than anything?
- What’s something you don’t normally tell people you’ve just met? (I’ll go first if you want.)
- What would your friends warn me about?
- What makes you feel most alive?
- Do you have any dreams you still want to make real one day?
- How could we make this conversation more interesting/fun together? (Not that it isn’t.)
- What’s something many people get wrong about you?
- What’s something about you you think would surprise me?
- What do you love most about yourself?
- What are you grateful for lately?
- If you were fully allowed to brag, what would you brag about?
- Would you rather ___?
The following 3 were also on my list. I remember enjoying them a lot. But now that I’m 10 years older, they feel rather cheesy. I’m not sure if this is a shift in the culture, or a shift in my relationship to them, listing them regardless:
- What would an absolute perfect day look like for you?
- If you could make 3 wishes…
- If you were a fortune cookie, what would you say?
Questions to Invite Deeper Connection
Some of these I came up with. Some I found on the interwebs. Some I borrowed from card decks or from Authentic Relating, Circling, and other connection practices.
I credited people/modalities wherever I remember who came up with it. I’m likely missing some. If one of these is uniquely yours, do let me know and I’ll credit you.
- What’s a value you wished more people held in high regard?
- To really know you, what would I have to know about you?
- What are you curious about right now?
- What’s something about you most people don’t get?
- What is life teaching you lately?
- What do you think you and I could have in common?
- What’s something you really want me to know about you? Why?
- What’s it like to be you right now? (discovered through Circling)
- What’s alive in you right now? (discovered through NVC)
- What could make this moment more wonderful? (discovered through NVC)
- How does this conversation feel to you right now?
- What do you really want to know about me?
- In an alternate reality, what would you and I be doing right now?
- What do you think I think about you? (from Sara Ness)
- If you could give 1 speech in front of the whole world, what would you say?
- What makes you feel safe and free?
- How do you think we’re different? How are we the same?
- What do you believe that many people consider crazy? (from Peter Thiel)
- If we never meet again, what would you want me to know? (discovered through ART International)
- What do you think you’re here to do in the world?
- How can I be here for you today?
- What’s your heart telling you right now?
- What’s something you wish people would tell you more often?
- What do you wish people talked about more often?
I wish you a lot of fun testing out these questions at your next social event.
Very different type of email today, so if you enjoyed these, do let me know. I still have lots of journals where more lists like these might be lurking.
If you have some questions you’d love to share with other readers, you are of course welcome to share those too.