Play once, watch your connections change forever.

The game to feel way closer to anyone by opening up the deeper side of each other.

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50,000+ customers play too

"I really didn’t think the prompts would be better than natural conversation but the framework really provided a special experience."

- Sterling ★★★★★

Play with anyone to build a closer bond.

Our team approached people in real time to play the game we made. They all loved it.

How it works

Break out of your routine of conversation...

level 1: Ice Breakers

Level 1 is all about breaking the ice, but they take a spin on your average conversation starters. They feel safer, yet still intimate.

level 2: Confessions

Level 2 Digs a bit deeper. Some fun, some real, and some getting things off your chest. These create bonding moments.

level 3: Getting Deep

How you see the side of someone you don't normally see. These transform relationships with deep understanding.

Wildcards

Challenges we keep secret until the game is yours. These bring out your wholesome side.

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HOW DEEP WILL YOU GO? Original

HOW DEEP WILL YOU GO? Original

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Original helps you have those special conversations where time flies and you feel incredibly close to someone in a new connection, an existing connection, or someone you love. We made the game after our viral social media series testing different kinds of deep questions and challenges until we came down to the 99 that made a difference. Some are fun, some are uncomfortable, but all of the game strengthens your bond with anyone you play with.

99 question and challenge cards

✓ for existing and new relationships

✓ you win by connecting deeper

Regular price $50.00 CAD
Regular price Sale price $50.00 CAD
Sale Sold out
Shipping calculated at checkout.

featuring..

  • 90 questions to open up split into 3 levels
  • 9 wildcards we keep secret until the game is yours
  • Simple Instructions included (only 2 rules)
  • 2-8 players (play with anyone)

shipping info

Domestic Orders (US)

Orders will be fulfilled within 1-3 business days and will ship depending on what service you select. Typically 5-10 business days.

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.

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These questions make a difference.

In 2022, we started something special. We asked people everywhere to have real, deep talks with each other. What we found changed us.

The best way to really know someone isn't through small talk. It's through their stories.. The funny little things that make them smile, the hard times that made them stronger, the lessons they'll never forget, and the memories they hold close to their heart.

But we noticed something amazing. When we turned these deep conversations into a game, people opened up in ways we never expected. Those big, important questions that usually feel scary? They became easier when it felt like play. Suddenly, sharing your story felt natural, even exciting.

It turned into something beautiful. A simple way to deeply know the people in your life. Because when phones are down and stories are flowing, that's when real connections happen. That's when we remember what it feels like to be truly heard and understood.

Sometimes the simplest things, like asking the right question at the right time, can bring people closer than ever before.

50,000+ play too..

This is their experience:

Popular Questions

Why is it so expensive?

For all the people you love in your life and the ones who aren't yet in it, is worth improving each one of these relationships for less than the cost of a night out?

How is this different from other card games?

None of the other games went through a process like ours. We built a social media brand asking everyday people meaningful questions they have never been asked before.

From our videos we got thousands of messages from people telling us how impactful it was to them as a viewer. We were told it was therapeutic and wholesome, and it made people feel good. Before we knew it, everyone was asking us for the questions, and our volunteers remembered us years later..

So we sat down, sifted through hundreds of questions to condense it into 99 question cards and wildcards that help you have a feeling of closeness you never felt.

We created a physical representation of the experiences we were creating; shared vulnerability that brings you closer.

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?

UPDATED: To help you feel confident with your purchase, we promise this game will help you open up and feel deeply connected with every single person you play it with. If you hate it, tell us we suck, get a refund, and you get to keep it for free.

How deep does this really go?

Most reviews say it goes deeper than they could have imagined. Some even call it life changing. We might need to come out with a box of tissues.

  • With the game:

    • easily get to know someone new
    • nourish your existing connections
    • create more memories
    • make opening up easy
  • Without the game:

    • same conversations over and over
    • connections don't grow
    • stay feeling disconnected
    • avoid needed conversations

OUR GUARANTEE:

We promise this game will help you open up and feel deeply connected with every single person you play it with. If you hate it, tell us we suck, get a refund, and you get to keep it for free.