It started with two cheap chairs, a Google Doc, and a sign.
How three brothers and two best friends inspired millions to go deeper.
It started with strangers.
We'd walk up to people we'd never met and ask if they wanted to do a challenge. We called it “How Deep Will You Go” because we liked the idea of not knowing what was about to happen.
Before the first question, we agreed on two rules together: dig deep, seek discomfort.
Everyone started nervous at level 1. Then the questions got deeper each round, and so did the conversation.
And as we did this in a video series, something kept happening. People would remember us years later, just from that one conversation.
Like Tay from Troy University, Caden from LSU, and Ayub from UCLA.
All it took was 20 minutes.
We kept getting to know strangers with our framework because it became addicting. Within about twenty minutes, strangers were telling us things their best friends didn't know, and we were sharing things ours didn't either.
The video with Emily, Taylor, and Stain reached 22 million views. People weren't watching us. They were watching three people who didn't know each other talk until the sun went down.
Then everyone asked for “the list.”
Everyone wanted our secret. Our list of questions. We had a Google Doc with hundreds of questions from the different colleges we did our experiment with.
We were getting hundreds of DMs a day. People would recognize us and thank us for "what we do." We didn't know it yet, but we were creating people's favorite conversations ever.
So when people asked us to help them connect, we made a game to do it.
The first prototype became core memories.
The most memorable time I played our prototype was with a stranger named Nicole. We sat on the grass for about an hour, talking about things you'd normally only talk about with your best friend. Afterward, she wrote about it:
"I would have never thought that a simple card game and conversation with a random stranger would change my outlook on life so much."Nicole
1,000 games. Gone in 5 hours.
We made the first run ourselves, packed orders from our mom's house, and chose literally every component. The material. The color. The fonts. The instructions booklet. The shrink wrap.
We printed 1,000 games. They sold out in 5 hours. It felt like a message turning into a movement. People loved getting uncomfortable to go deeper in their relationships, because deep down, we all want more meaning.
Built from real conversations, not a list.
Every question was shaped by talking with over a thousand real people. We saw which phrasings made someone light up and which ones fell flat.
We sat over questions for an hour trying to find a way to make them sound more human. We read psychology books to understand the kinds of questions that get people to open up.
We also learned how to structure a conversation in a way where going deeper just feels like the right next step. Building a connection deeper than you ever have was easy.
Every game started with something.
Each one began with something we couldn't stop thinking about. Even the colors have meaning behind them.
Original
The game thousands begged us to make. Black, for how deep it goes.
Shop Original
For Lovers
A lack of vulnerable conversations kills relationships, so we made them fun. Dark blue, to represent deep, committed love.
Shop For Lovers
For Dating
What would happen if a date was a game where you both answer the same questions? Burnt orange, like a sunset.
Shop For Dating
For Families
We wanted to get closer to our family, but didn't know how to start. Yellow, our mom's favorite color.
Shop For Families
2nd Edition Founders' favorite
You kept asking for more questions. Just like Original, but with all new ones.
Shop 2nd EditionEveryone wants to connect on a soul level. Our games are how.
You begin every game agreeing on rules to set the vibe. You pick from level one not knowing what comes next, and by level three, you realize you're telling a story you didn't remember until just now. By the end, you can't believe how fast time flew by. You feel so seen, so understood, so known. Just from a simple game.
We love deepening relationships. This is how we show it.
200,000 games later.
"me and my friend stayed up all night talking and we didn't even realize it until the sun came up"
"We have all been friends for at least 20 years but we still learned so much about each other."
"We didn't know each other, but we felt safe... I talked about things I had never talked about even with my best friends"
"...we've been married for 40 some years, and I'm still learning things about him."
"i've never seen my mom open up so easily"
"I hate calling this a game because it isn't. You both win. Every time."
We're the 5 creators.
How Deep Will You Go is built by three brothers and two best friends.
Stain
Storyteller
Cody
Head of People & Progress
Brandon
Storyteller
Ledarius and Kyvon capture people's stories with our games, from IRL moments to helping customers.
Ledarius
Stories and community
Kyvon
Stories and community
Now it's yours.
Everyone has a side of them you've never seen. Our games help you find it.
Find your game