For Your Next Dinner Party
On starting a meaningful conversation
Spring Cleaning is a newsletter delivered straight to your inbox (or the Substack app) where I share personal essays, recommendations, and ideas on how to live a joyful and intentional life. My hope is that it brings a mini moment of reflection to your day. 💌
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There is nothing that makes me feel more 30 years old than a dinner party. I love hosting, planning a menu, looking at tablescapes, and fantasizing about the themed parties I’ll have in my future backyard (a tea party and summer solstice party are first on my list). But as much as I love homemade food and a good cocktail, it's the connection that I value the most. Some of the most memorable and intimate conversations with both new and old friends have usually happened around someone’s dining room table.
I recently listened to this episode of Plain English that discusses the principles of having an emotionally resonant conversation (go listen!). One thing that made the biggest impression on me was the distinction between shallow and deep questions: a deep question is one that asks - directly or indirectly - about your values, beliefs, or experiences. For example, if you learn that someone is a lawyer, a deep question might be “what made you go to law school?” Or, “would you tell one of your kids to become a lawyer?” As I meet new people and attempt to strengthen my existing relationships, these guidelines have helped me dive deeper.
Like so many of us, I’ve always disliked the surface-level, sometimes meaningless conversations we have with people we see infrequently or don’t know very well. Post-pandemic, I’ve become more socially anxious and anticipating these conversations often fills me with dread. I’ve been guilty of avoiding saying hi to people that I know but haven’t seen in years because I think the conversation could be awkward, that I might overshare, or won’t know what to talk about. This was never the case before 2020 - has anyone else experienced this? Perhaps it’s just part of getting older and navigating the nostalgia and strangeness of not knowing people who were once in your orbit.
I felt inspired to write this today because a) I went to a new-ish friend’s house for dinner last night and b) I recently saw a college acquaintance and we got into a very deep and meaningful conversation. In just 45-minutes, I learned more about this person than I did in four years and discovered many parallels in our experiences and values. This brief moment of connection was a much-needed reminder that it’s not always scary to rekindle with old friends and acquaintances.
In the spirit of more meaningful and intimate relationships, I wanted to share a list of my favorite conversation starters that I’ve compiled over the years (re: my obsession with the Notes app). Use these questions for your next dinner party, when you’re spending time with a new friend, or you want to go deeper in your existing relationships.
My favorite questions
I loosely organized these by the closeness of the relationship, but I also think you could ask some of the more intimate questions to a new friend and vice versa!
What category would you sweep in Jeopardy?
If you had to give a TED talk, what would you talk about?
What’s something as an adult that you don’t understand but absolutely should (e.g., taxes)?
What is a food you wish you could experience again for the first time?
What random skill did you acquire from a job in high school or college?
What hobbies do you wish you had more time for?
What ingredient would you be in a salad?
What are the top 3 features of your dream house?
What’s a job you know you’d be great at even though you have no experience?
What’s your childhood comfort food?
Who is the most interesting person you’ve ever met, and why?
If you were to go back to college again, what would your major be?
(Think Día de los Muertos) - what objects would be on your altar to bring you back to this world?
Would you rather have dinner with your great great grandkids or great great grandparents?
Which of the seven deadly sins is yours?
If you could relive one year of your life, which year would it be and why?
What do you think about when you’re falling asleep?
You’re writing a book - what is the title of the chapter of life you’re in right now?
What’s the next chapter called?
What are you a beginner at?
What’s something you hate that you wished you loved?
If you could go back to earth for a day - and can’t interact with friends or family - where would you go?
What is the last thing that cost you nothing but made you happy?
What’s the most meaningful compliment you’ve ever received?
What is one day you’d relive for yourself and not change anything about it?
What’s one talent you wish you had for your own joy? (Not to monetize)
What’s a mistake you’ve made that’s changed your life for the better?
If you got a call from the police right now saying I got arrested, what crime would you think I committed? 😂
What’s something you’ve changed your mind about over the last year and why?
If I were to lose all memory, what’s the one memory of ours you’d tell me about?
In the same vein, I wrote a post late last year on questions to go deeper with your parents or loved ones. You can read that here! Are there any questions I should add? Leave your favorites in the comments 😊
Sparking joy this week
💜 Lilac season
👭 Seeing old best friends
👩🌾 Volunteering at my community garden
🍓 Strawberries are here!
🥐 Treats from my favorite DC bakery
🌱 Watching my new plant grow (she is thriving!!)
This week’s loves
Lots of listening this week. I loved Ezra Klein's interview with Salman Rushdie - it made me reflect on how we perceive people online and the challenges of social media. I also discovered a new (to me) show called Empire that I’m obsessed with. As the name suggests, the show explores the stories, people, and events of major empires over the course of history. I’ve already listened to the two-part series on Cleopatra and Isabelle of Castile and I’m working my way through several episodes on the history of the Ottoman empire. I highly recommend this show if you love history and/or interesting stories! The hosts make 1,000 year-old events engaging, interesting, and fun. I enjoyed this episode of Plain English and the slightly controversial conversation on the relationships between smartphones and teen mental health.
Reading Horse by Geraldine Brooks. I’m only 150 pages in, but I’m really enjoying it so far! Would recommend.
Cooking this coconut-poached fish from NYT cooking. This is a simple and restaurant quality recipe - make it ASAP!
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Thank you so much for reading! I deeply appreciate each and every one of you. Spring is here! 🌸 x
Love this! At one point someone published a list of “30 questions to fall in love” (or something like that) and I love going through those questions with friends!
LOVE these questions! I've recently been reconnecting with an old friend from college and find myself wanting to go deeper and emotionally connect (over text) but have been so stuck! I'm adding these questions to my Notes app!
One question I did come across recently is:
Where do you feel most at home? Do you think we are rooted in certain places?
Also -- you've convinced me to listen to Plain English!