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HOW DEEP WILL YOU GO? 2nd Edition

HOW DEEP WILL YOU GO? 2nd Edition

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HDWYG 2.0 is the highly anticipated sequel to our viral conversation game, made from thousands of real stories of connection and breakthrough moments. It's designed for friends, partners, family members, or even self-reflection, who want to experience those rare conversations where time stands still and you discover things about each other you never knew existed. Now reimagined with more powerful prompts based on real player experiences, this game helps you break through small talk and experience the kind of closeness you crave.

✓ 99 new open-ended question and challenge cards

✓ for existing and new relationships

✓ just like the original: you win by connecting deeper

Regular price $34.99 USD
Regular price Sale price $34.99 USD
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.

View full details

Second Edition works with anyone

We are on a mission to deepen human connection. Kyvon from our team tested it with strangers to keep it unbiased and they all loved the experience.

"I hate small talk, thank you for this experience"

- girl from the video (us too)

Create deep talks that become core memories.

Remember when we used to talk for hours? Not through screens, but face to face. Sharing stories, dreams, and laughter until we lost track of time?

These days, we're all stuck in our phones, feeling more alone than ever. We scroll and scroll, but something's missing.. That real human connection that makes life fulfilling.

The best conversations aren't about small talk. They're about sharing what makes you you.. Your favorite memories, the times your heart was broken, the lessons that changed your life. We perfected these deep talks.

When you're playing the game, the hard questions become easier to ask. The real stories start flowing. And suddenly, you're learning things about someone you never knew before.

This Second Edition brings new questions and challenges that do what our first game did, but even better. It helps you put down your phone, look up, and remember what it feels like to truly connect with someone.

Because at the end of the day, that's what we're all looking for – to feel closer, to understand each other, and to be understood.

How it works

Breaking 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 different.

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.

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 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.

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.