Original


99 questions you wouldn’t think to ask that deepen your connection with anyone. Organized across 3 levels to make deep conversation feel natural. It doesn’t feel like a game; it feels like discovering a side of someone they always hoped you’d find.


$50.00
  • 100,000+ people love playing
  • Makes a perfect gift everyone loves
  • Perfect for coffee dates, deep talks, and get-togethers 
30-Day Hassle Free Returns
100% Money-Back Guarantee
Sam

I can't explain how valuable this game actually is. Absolutely worth it, and am desperate to play again.

About 50% love to pair with..

2nd Edition
2nd Edition
Like the original, but with all new content.
$71.00
FAST SHIPPING
THOUGHTFULLY DESIGNED
FAST SHIPPING
THOUGHTFULLY DESIGNED
FAST SHIPPING
THOUGHTFULLY DESIGNED
FAST SHIPPING
THOUGHTFULLY DESIGNED

This Game Started By Accident

Viral public interviews

Viral public interviews

We hosted THOUSANDS of public interviews using new questions every time.

Everyone begs for the list

Everyone begs for the list

Everyone started asking for our list of questions because they said the experience felt so healing.

So we made the game

So we made the game

We carefully chose the 99 best prompts out of hundreds we tested.

Tested it with strangers

Tested it with strangers

We had a theory that our game was a cheat code for creating comfort in vulnerability in an instant. Turns out, we were right.

Now 100,000+ play

Now 100,000+ play

We have a huge community of people who bring this game with them wherever a conversation may happen :)

4 levels that soften the mood

Ice Breakers

Ice Breakers

go past small talk

Confessions

Confessions

where more vulnerability shows

Getting Deep

Getting Deep

where you really feel seen

Challenge

Challenge

Wholesome and fun challenges

Hype you can trust.

Here are the numbers:

Hype you can trust.

Here are the numbers:

0k+

growing deeper relationships

0%

5-star reviews when we ask

9/10

9/10 people light up when they play with us

* Based on internal studies and customer feedback surveys.

Carefully & Intentionally Made

How we compare to others

Carefully & Intentionally Made

How we compare to others

Original
Original
Others
progressive levels that go deeper as you play
Emotionally intelligent cards
created by best friends of 5+ years
online community of 1 million+ people
on a mission to deepen human connection
Aesthetic, high quality minimal design

Here's the FAQ

Find answers to questions about our products, shipping, returns, and more.

Who do 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.

How can I contact 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 refund policy? +

Yes. We guarantee our game will spark your favorite conversations. Try it with a few people, and if it doesn't deliver memorable moments, simply request a refund. Jo, our customer happiness manager, will take care of you.

We will not accept exchanges after 30 days of your delivery date.

What payment methods do you accept? +

We accept major credit cards, PayPal, Shop Pay, and Apple Pay for your convenience and security.

How deep does this 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.

How can I contact support? +

If you want to get in touch, email team@howdeepwillyougo.com

Do you have a refund policy? +

Yes. We guarantee our game will spark your favorite conversations. Try it with a few people, and if it doesn't deliver memorable moments, simply request a refund. Jo, our customer happiness manager, will take care of you.

We will not accept exchanges after 30 days of your delivery date.

How deep does this 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.

Money-Back Guarantee

You’ll love playing this game more than your normal conversations, and if you don’t, we will refund you.

BUY NOW
100% Satisfaction
Fast Shipping
Easy Returns

Money-Back Guarantee

You’ll love playing this game more than your normal conversations, and if you don’t, we will refund you.

BUY NOW
100% Satisfaction
Fast Shipping
Easy Returns