Gianna’s Glimmer - No More Bad Conversation. Magic Questions and more.
Hi there,
I just got back from a family vacation in Napa, and one of the small things I packed ended up being one of the best things I packed: a deck of conversation cards for dinner every night.
One evening, our waiter noticed the deck on the table and asked what they were. I told him they're a great way to spark conversation, learn something new about the people you're with, and stretch your imagination at the same time, rather than defaulting to the same dinner-table small talk. Then we pulled a card and asked him the question: What movie would you never want to watch twice?
He lit up thinking about and then sharing his answer. And we felt like we got to know him a little bit better…as a human.
Gianna's Gem: The right question at the right moment can turn a transactional interaction into a memorable one. It costs nothing and takes ten seconds to ask. It creates engagement and inclusivity and a little spontaneous surprise and delight.
Priya Parker, author of The Art of Gathering, has a name for questions like this. She calls them "magical questions." Her definition: a question is magical when everyone in the group is interested in answering it, and everyone is curious to hear everyone else's answer. It's a simple equation, but it's the difference between a question that lands and one that falls flat.
The questions that don't work are the ones we default to on autopilot: How are the kids? How's work? Anything new? They're not bad questions, they're just tired. They invite a status update, not a story.
Magical questions do something different. They invite a story instead of an opinion, and in doing so, they let people show up as more than their job title or their role in the room.
A few of my favorites to keep in your back pocket:
What is one thing you own that probably nobody else in this room owns?
What's the first concert you ever went to, and who took you?
What's a path you almost took but didn't?
What topic could you give a 20-minute talk on with zero preparation?
Before your next dinner party, networking coffee, or kid's school pickup line conversation, bring one or two of these with you. The moment conversation starts to lag, that's your cue. I often throw a few in my purse and even use them if I’m out entertaining a few of my sons friends - they love it and we all end up with a few laughs as well. For dinner parties, you can also slip a couple under everyone’s plate and it creates a way for people to actively engage and ask questions that are prepared in advance and spark group conversation.
Gianna's Gem: You don't need to wait for conversation to get interesting on its own. You can simply bring the spark with you.
But the magical question is not the only way to spark better conversation. Here are a few other gems I use regularly to keep conversation engaging and playful:
1. Co-create a scavenger hunt. If you're on a group trip, build a list together before you go (or on the first day together) and require photo proof along the way. In Napa, our family hunted for things like pink hair, a bride, a skateboard, a Ferrari, a grasshopper, a balloon, a hummingbird, etc. It kept everyone looking up and around instead of down at a phone, and it added just enough friendly competition to make people pay attention to the place they were actually in.
2. Pair the meal with an experience. Don't just plan a dinner. Plan a dinner after something: forest bathing, a wine tasting, a painting class, a friendly poker game. Conversation flows so much more easily when people have already shared an experience together. You're not starting from zero, you're picking up a thread that's already there.
3. Ask everyone to bring something to share that’s under $50. Fancy sun lotion or hand cream to share. A genuine compliment. A square of good dark chocolate. A bottle of wine. Even a joke or a compliment. It doesn't matter what it is, what matters is that everyone gets to give and receive. People leave feeling like they contributed to something, not just attended it.
Stack these all together, and your magical question isn't doing all the work alone at a quiet table. It's landing on a group that's already warmed up, present, and a little more generous with each other than when they arrived.
XX,
Gianna
What I'm Loving This Week: Good Humans Example
A New Baby Care Package…But for the Neighbors, not the new parents
Our favorite next door neighbors just welcomed a newborn, and of course, we sent over goodies to welcome the baby. What I didn't expect was what came back: a basket from them, for us, with wine, earplugs, and under-eye patches, along with a note written "from the baby" apologizing in advance for any crying we might hear through the walls.
I was so delighted by the thoughtfulness, I haven't stopped talking about it. It flipped the script entirely. The new parents, who have every excuse to be depleted right now, took a moment to think about our experience too.
Everyone should be this thoughtful. Consider this your nudge: if a neighbor welcomes a baby, a little something for the people who'll be living next door to the new noise might be the most memorable gift you give all year.
Gianna’s Gems is a weekly exploration of ideas that transform the ordinary into the extraordinary. If you found this valuable, please share it with a fellow magic-maker, and subscribe for more inspiration delivered directly to your inbox.
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