36 Questions With a Stranger

The event we almost canceled and why it was our most successful yet

“I wasn’t sure of the setting or the format...the ambiguity made me nervous.”

-Eli Kerr, Owner of Gnarly: Clean Sports Nutrition
Attended TheHouse.org’s inaugural 36 Questions With a Stranger in February 2018

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When we read an article in The New York Times about how researchers explored 36 questions they thought could accelerate getting to know someone intimately, we knew we had to test it out in our own community. What if we gathered a group of 40 strangers and asked them to get vulnerable with someone they had never met before?

Would anyone show up? Were people willing to be vulnerable, to open up, and to wear their hearts and thoughts on their sleeves?

People bailed. Lots of people. And we were ready to cancel.

Some guests had legitimate scheduling conflicts arise and others, honestly, were nervous about getting vulnerable with a stranger. We couldn’t blame them. We weren’t sure if it would work either.

After rallying our own morale and faith in the concept, we made one more round of hefty invites the day before the event. Our guest list went back up to 36 people. We bought twinkle lights, re-confirmed with the caterer and bartender, and crossed our fingers.

Going to an event where you don’t know even one person “always takes a good amount of courage.”

-Eli Kerr

PEOPLE WITH COURAGE: How Awkward Transformed Into Connection

As guests started to hesitantly (understatement of the year) began to arrive, we greeted them with all our enthusiasm, gratitude, and a name tag that had a character trait written on it that we had made beforehand. People helped themselves to drinks, food, and the usual awkward party conversations with strangers. They were nervous. We were nervous. But, man, we sure were happy to have everyone there.

After 30 minutes, we told people to find their character trait synonym in the group to find out who they would be spending the next 45 minutes with, getting to know he/she intimately. Generous had to find Kind; Funny had to find Hilarious; Happy had to find Joy.

They found each other, and each pair found a cozy corner to sit down with each other. We told them the rules, which are simple: there are 36 questions, divided up into three sections of twelve, and they would only have 15 minutes per set.

Ready. Set. Connect!

When People Didn’t Want to Stop

“Once the space is created, people will take over and naturally get to know each other.”

-Eli Kerr

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As soon as the first question was asked, the room filled with easily-flowing conversations. Turns out, it’s the thought of being vulnerable that is scary. Once you take the plunge and simply show up, ready to be real, the rest is easy. It is a difficult thing to get people to stop talking when they are allowed to witness and to be seen by another.

I quickly found out that keeping time for the group wasn’t the most popular responsibility of the evening. Every time I yelled out my two-minute warning, there were pleas for more time and slight scowls on people’s faces.

Some of the most vulnerable questions included:

• When did you last sing to yourself? To someone else?
• Do you have a secret hunch about how you will die?
• What is your most treasured memory?
• What is your most terrible memory?
• Tell your partner something you like about them already.
• If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

Now you can see why people may have been nervous about coming to our event. These are questions and answers and thoughts that we don’t really think about, give much time, or want to share with anyone, let alone a stranger.

Impromptu After-Gathering

We eventually had to vacate the venue as the night was getting late. No one wanted to stop talking. People were saying they had met another soul mate, a new best friend, and everyone was hesitant to leave. In just 45 minutes, connection happened when people got real and vulnerable.

The crowd of 36 people left the venue and walked two blocks to a local bar to continue their conversations. Many of us are still in touch, and one group took the 36 questions to their friends’ brunch gathering the following morning. The event was a much-needed dose of real human connection.

And we almost canceled this event. We’re so glad we were vulnerable and kept the doors open.


Our mission is to create more joy and less suffering through human connection:

“Our sense of well-being depends to some extent on others regarding us as a You; our yearning for connection is a primal human need, minimally for a cushion for survival. Today the neural echo of that need heightens our sensitivity to the difference between It and You—and makes us feel social rejection as deeply as physical pain.”

-Daniel Goleman, Social Intelligence: The New Science of Human Relationships