The Connection Experiment: AI Edition (Nov 7, Online)

We are hosting an evening of real conversation, and this time we're testing a themed night. More and more of us are talking to AI, sometimes telling it things we haven’t told anyone. Does it leave you feeling understood? Or a little more alone?

The public conversation about AI is about investment, education, and a frictionless future. At work, it can feel like everyone is expected to keep up. There’s rarely a space to look inward and ask what this technology is stirring up inside us: fear, loneliness, excitement, or all of it at once.

From the first gadget that felt like magic to the AI we use today, this is an evening to share those feelings with another human being, and to ask how we stay human in the middle of it. Whether you’re a tech expert or have barely used AI, you’re welcome here. No debates, just your own experience, shared with a stranger who is doing the same.

Since our first online session in August, over 2000 people have signed up for our events, and most of the room stayed past the official end just to keep talking.

What to Expect 🪑
You’ll spend 1 hour in paired video conversations with people you haven’t met yet. Here’s how it works:

• You’ll be matched into breakout pairs with 3 different people over the session 🔄
• Each pair gets ~12 minutes and a thoughtful question to explore together 💭
• You’ll both ask AND answer, equal time, full attention 👂
• Camera on is encouraged but optional — full presence either way
• You’ll get the question list right at the beginning of the event. Start anywhere, skip anything that doesn’t feel right.

A taste of the questions 💬
We’ll start with memories and move toward the present, with both light and deep questions to choose from:

• When did you first hear about AI, and how did you feel the first time you used it?
• Do you talk about personal things with AI? Has there ever been a moment when AI made you feel understood?
• If AI eventually becomes impossible to tell apart from a person, in writing, in conversation, what do you think would still be valuable about being human?

Why We’re Gathering 🌱
In a world where we’re more “connected” than ever, genuine conversation has become surprisingly rare. This isn’t about networking or problem-solving. It’s about something simpler: the experience of truly listening and being heard. Here’s what some past attendees said:

• “I signed up just to kill some time, and I was pleasantly surprised.”
• “Very easy to turn a stranger into a friend”
• “I don’t have anybody to tell my day to. As much as people are now talking to their AIs, I still think there’s a huge value in connecting with people”

Can’t make it? 💛
Spots fill quickly and many people are waiting. If your plans change, please update your RSVP so someone else can join.

Want more? ✨
This free session is a one-hour taste. For longer conversations in a smaller room with a guaranteed spot, check out our meetup page for paid in person/online events.

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