







Not your typical "deep question game"
Three years ago, we started a social media series asking people questions nobody had ever asked them before.
People loved opening up more than they ever have, all through a simple game we'd created on Google Docs.
What looks like a simple card game is the bridge many of us have been searching for—a way back to each other in a world that keeps pulling us apart.
And the success of our Original game took us by surprise. As more and more people experienced these profound connections, we kept hearing:
"We need more questions!"
"Better than the ones in Target!"
So we listened, gathered what the people liked and didn't like, and crafted 99 new questions that take the experience even further—helping you discover new depths in the people you thought you already knew.
"In a world that seems often too fast, chaotic, and troubled I welcomed this game as a way to create connection and to build community with those I care for."
- Cameron ★★★★★
Three levels. Endless connecting moments
"I found the questions to be really engaging"
- Jacob

Ice Breakers: not the boring ones
From the highlight of your day to the song you'd play with 5 minutes left to live

Confessions: what you've been wanting to say
From an experience that impacted you more than expected to a sentence you regret saying

Getting deep: share your deeper story
From a feeling you miss to the apology you never got to give

Secret connecting challenges
Sorry, but just like the Orginal we keep these secret. Don't worry.. they are wholesome.
Takes about 3 minutes to learn
The game is simple. The 2 rules are:
- Dig deep
- Seek discomfort
Whoever brought up the game starts as Player A. Player A picks a card, answers it, then asks the other player the question.
This process repeats for each players. Once a card is drawn from each level, a challenge card can be drawn.
Play until deep connection arises (some people end up playing 12+ hours)
2.0 compared to...

Questions that are engaging
Cringe ChatGPT questions
Nobody wins, everyone connects
Someone wins, making vibes weird
Goes deeper where you feel connected
Doesn't go deep the way you want
Made by people and customer feedback
Made by a lame marketing team

It's fun, addicting, and deep
"Since playing, I feel my bond and connection with my friends has grown stronger."
- Olivia ★★★★★
What happens when you play our games?
Let them tell you:
Popular Questions
Why is it so expensive?
Our games aren't your typical dollar store games. We design our products to last for years so you can play over and over again. The cards are high quality and the design is sleek. It's like that one piece of clothing with a hundred memories attached to it. There's so much depth.
How is this version different from Original?
Second Edition is just like the original, but the questions are more specific and unpredictable, making it super fun. Our original game is already amazing, but this one is based on customer feedback. You should try it ;)
Who can I play this with?
Play with anyone. If you look at our reviews you will see people playing the game with friends, strangers, lovers, family, siblings, you name it.
Any tips?
Follow the two rules.
How do I get in contact with support?
If you want to get in touch, email team@howdeepwillyougo.com.
When will my order be shipped?
Domestic Orders (US)
Orders will be fulfilled within 1-3 business days and will ship depending on what service you select.
International Orders
For international orders, there may be import costs to the shipping carrier, such as duties, import taxes, or brokerage/disbursement fees upon delivery which the customer is responsible for paying. Shipping times may also be longer than expected.
Do you have a return/exchange policy?
All sales are final, but of course, we will exchange your order if it comes in damaged. Just send us an email at team@howdeepwillyougo.com so we can help you out.
We will not accept exchanges after 30 days of your delivery date.