How Deep Will You Go? Original *PRE-ORDER*

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Regular price $35.00 Sale price$27.99
Shipping calculated at checkout.
(Pre-Orders are NOT guaranteed to ship before Christmas, but if there’s a perfect gift to have after the holidays, this is it)
  • In stock, ready to ship
  • Inventory on the way

Easy-to-play conversation card deck to deepen your connections and become a lasting memory. It’s for those who desire better friendships, deeper relationships, and connections that feel true to the soul.

The compact size of the box makes it perfect for taking on the go, making meaningful conversations effortless, anywhere.

Whether used solo as journaling prompts to understand yourself, playing with friends or family, on a date, or even with strangers, a deeper connection will arise.

HDWYG? - Three levels of carefully crafted question cards to dig deeper.

  • 99 Question Cards and Wildcards
  • Instructions included
  • 2-8 players
  • new core memories included
For international orders, additional local import charges may be applied. Shipping times may also take longer than expected. Please check in advance to avoid any surprises.

Level 1: Ice Breakers

These break the ice, but in a way you wouldn’t expect. They take a spin on your average icebreaker questions.

Level 2: Confessions

These dig a bit deeper. Some fun, some real, and some to get things off your chest. They are the kind of confessions that actually feel good to let out.

Level 3: Getting Deep

These questions take meaningful conversations to the next level with a mix of questions you wish you were asked and questions you have never been asked before. This is how you really learn about someone in a meaningful way.


These are optional, but they elevate the experience to embody what deep connection really feels like. We keep these a secret. 

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.

how it works


Level 1 is all about breaking the ice, but better. They take a spin on your average icebreaker questions.


Level 2 digs a bit deeper. Some fun, some real, and some getting things off your chest.


Level 3 is all about getting deep. These are how you learn about someone in a meaningful way.


These embody what deep connection really feels like. We keep these secret.


core memories are made, trust is built, and building a bond with someone never felt so easy.

meet someone new
build a brotherhood
journal to yourself
connect outside
use on date night
start a connection

"be raw and honest, how was it?"

The game is amazing bro. I've actually been thinking a lot about why I was able to open up to you guys so easily. I kinda realized when these insanely deep and thought provoking questions are framed as a "game" they become much less intimidating. Because I thought of it as playing a game, I subconsciously was able to let my guard down and was more open to answering the questions even though these are topics of conversation I'd usually try to avoid with my closest friends. It's really an amazing way to get to know people and spark those deep conversations with the people you love.

Noah H.

The game is a lot of fun and a great way to break the ice with new friends as well as get deep into your feelings with old ones. It leads to awesome conversations and just helps you talk about the feelings you might not ever realize you are experiencing.

Emily P.

When we played it, I felt like grew closer to the people around me even though we were already pretty close. It put me in an environment where I felt positive energy. It would be interesting to play with a group of individuals that I do not know. It’s a great game.

Noah K.

short and sweet:

When you start playing it becomes less about the game and so much more about the people you play it with and their stories.


I made 4 people cry and got to see a side of them I never have seen before it is amazing.


I absolutely love this game! I highly recommend it to everyone that I come across, it is a must have in your collection of games!


It was AMAZING!!!


It is amazing thanks so much for the fun and for getting to know my friends even more.


It was so much fun! I even played with my therapist who loved it and wants to get it as well! Thanks:)


The game is amazing and I love how easy it is to play and just overall great for getting closer with others.


Amazing!!!! We still haven't gone through all the cards though.


It helps me bring out a side of me I always wanted to let go of but never could.


F*cking amazing.


a bit deeper:

Felt like I was stepping into a different version of myself and my friends felt the same. Bonds became closer because of it and thankful we've grown with each other through this game!


Phenomenal! You can tell that a high degree of intentionality was put into it. Not only in the questions but even in the quality of the cards. Great work.


I loved it. The way the cards are sectioned out in the different colors was awesome. From there the questions that were thought of for each category made it really easy. This was really fun to play and have some really good conversations off of it.


It's awesome! We love playing a couple rounds in the evening or right before bed. Gives us a chance to talk and learn things about each other.


Its amazing! A lot of the questions really make you think for an answer and makes you learn a lot more about a person as well as yourself.


It is honestly a really impressive game! I'm very happy with almost 100 high quality questions that make me think for hours even after the game. It's so good I don't want to burnout so I gotta watch out how much I play with friends.


It was extremely insightful. I played this game with my family and was able to learn so much about them. I also played it alone and was able to learn and understand more about myself. It was a great learning experience and was very interesting. Honestly, it's an amazing game!


It's fun. Its amazing. It helps pull people out of the normal conversations and really get deep. It allows you to start conversations that you normally wouldn't and from there you see people at their most vulnerable most raw state of real. Not only does it allow a vent for them but it allows you to vent as well. Great game.


it was very intriguing and involving. I've never had an experience like this before and its definitely one of the best ways to get closer to people and leave a connection open with people.


I was able to play it! Has a lot of fun and was able to get to know more about the people around me. Definitely playing it again in the future.


even deeper:

To be raw I enjoy the game a lot. We live in a society where everyone is taught to only see the surface level of things, to just know facts instead of actually understanding anything. That's why when you ask anybody about anything you quickly see how little of everything we know. This is a change of energy to give the person a opportunity to be listened to and not to just talk and talk like everybody wants to do. Depth and understanding ourselves helps better live in life. All in all I love it.


The game is absolutely amazing. You get closer with everyone who plays even those you thought you already knew everything about. The thought put in behind the questions just makes it an absolute necessity if you struggle getting a deep, powerful connection with people, and it makes it much more comfortable to play with others because it's just a game. Absolute 12/10 amazing work.


I love it so much man. It's given me an outlet to unlock my true inner self in a way. There's been some things that I've been holding in for a couple years, and playing this game with my friends and family has allowed me to release some heavy weight that I've had on my shoulders. It just makes me feel like a new person, and it's just so crazy to me the time and effort in creating these questions, because every single time I look and glance at these cards, I always have a new answer for each one. This game is a definite recommend, 10 out of 10.


It got very emotional and took some time to get everyone to fully open up, but without the game, none of what was said would've been said. Absolutely amazing game, I'm happy I could be one of the firsts to buy and play it.


It was great! I played it with a few family members and friends I don't really have much conversation with and the amount of layers we were able to unpack in a conversation was incredible. It also helps me improve my communication skills and talking to others in a humble, raw, and open way. 


Oh my goodness. The game is phenomenal! It's so hard for me to even articulate the feelings and emotions that accumulated during the whole conversation. The best part about the game is how easy it made it for us to open up to each other even though the group I played it with wasn't even that close to begin with. The game single-handedly strengthened the bonds between all of us, and I am so thankful for it! Thank you for everything!


playing with friends:

I finally got the chance to play it with my friend last night! it was great. It sparked a lot of conversation and we both ended up sharing deeper things beyond the game. it was really nice!


Definitely have played it me and my  friends do a hangout every week and we played for at least 2 hours straight the other night it allowed me to open up to them in ways I haven't opened up to anyone In a long time and helped them and me better understand one another on such an emotional and vulnerable level. 10/10 game.


Guys it was sooooo much fun. Yesterday I played it with my best friend and a few more friends and we all loved sharing our thoughts and feelings. We went through every single question actually but it was sooo awesome and it's crazy hearing experiences and some insecurities other people have that you'd never expect or think about. It makes me realize a lot of people can relate to your feelings more than you think and I think this game made it really easy to open up about those things. I love it so much thanks guys.


It was amazing, truly strengthened friendships and really opened our eyes to each others lives.


It's been great! I've had the opportunity to play it with a few friends and we've been able to discuss things that we've all never really had the courage to talk to other people about. I also really enjoy the variety of depth that can be found within each level to help keep the engagement and vulnerability different and not overwhelming.


I played it over FaceTime with one of my friends, we had already known a lot about each other but I learned a little bit more. Love your game and the card design & texture. The appearance of the cards combined with the ability to connect with other people is such a great combination to me.


Awesome, really enjoyed reflecting and being introspective with my friends! Thank you so much :)


It was amazing!! I played with my best friend and we connected on a deeper level than we've ever had before. It made us both sob like crazy. It was also great to look within ourselves too.


It's a utter blast! I was playing with my friend of 10 years, and still learned some stuff that I didnt even know about them! I would definitely recommend this game!


I loved playing hdwyg! I've played it twice. Once with my sisters, where we got to know each other a little better, we even discovered things we hadn't known previously. The second time with a couple of friends, it sparked a real and intimate conversation where we got to be honest and transparent with each other. I LOVE this "game"!


more friends:

Absolutely amazing! I played it with my friend group and our relationship grew so much. I can't wait to play this with more friends and on dates! Thank you so much!!


These cards have been such a blessing for me and my friends, the bond that we never thought to have is finally here. I have played it with my aunts and have had to translate some of the cards into Spanish, they are very conservative minds and we can't believe how much they have shared. I also can't wait to share this amazing journey with my sisters once we get together. Thank you for providing such a quality game.


It was emotional. In a short preview game with my friend, I learned a lot—something we want to do with our other friends. I'm an open person, or I thought I was but this made me realize there are things about me that the closest people have no idea about. I figured it would be that way from the TikToks you guys make. It was awesome to experience that and it ended in one of the best hugs I've had in a while.


It was absolutely amazing truly, I played with two of my friends and our friendship grew closer and now we have more deeper conversations every time we talk. So I'd just like to say thank you, you guys have given me and my friends an experience that not many people can!


I love it and so do my friends, we've been getting to know each other more than we thought we already knew!


I loved it, I learned some things about my best friends I didn't know and I revealed my biggest regret. Overall I love it especially since I'm much more into deep talk then small talk.


It was great I got to know things about my friends that I never knew about and we both realized that we are very similar.


It was amazing! It helped me get close to my friends and family. It's a great way to dig deep and have an opportunity or chance to open up about things that are needed to be said. Thank you for the carefully crafted game.


with family & lovers:

It is a great game. I use it to play with my gf and they have amazing questions to get to know each other and all that stuff. I tend to use it with any other friends that come in my way in the future. 10/10 recommended purchase!!


To be honest, this game is amazing. I've already played it with my wife and 1 other friend and the convos we had were intentional, honest, and insightful. I love that it isn't your surface level "what's your favorite color" "how's the weather" experience. It forces you to grapple with the good, the bad, and the ugly.


I love it. There very great questions. Me and my boyfriend played it and my cousins her boyfriend played it.


Incredible and perfect for date night! Could play for hours!


It was awesome! My whole family finally got into deep conversations and got to interact with each other for the first time in a while!


It's been really cool because I played it with my cousin and even though we've known each other our whole lives we still learned something new about each other.


I was honestly amazed me how good the question were. I really enjoyed playing it with my girlfriend and I learned a lot more about her.


It was a great way to share and get a better understanding of what all my family is be feeling, since we had lost my brother last year in May, leaving his 5 kids and wife behind. Has help us express ourselves in a fun and caring way, thanks for this wonderful experience!!!


the skeptics:

It was actually so much better than I expected. Like me and my best friend play it every night, and it's helped us learn more about each other and we both feel like it's honestly made us a lot closer.


I am the oldest out of 8 kids and honestly, going into it, I didn't know how it was going to be. I played it with my family and we talked for hours, HOURS. The questions are perfect to get into those meaningful conversations. Definitely a recomend!


I've played it once so far, at first I was skeptical about it but I soon found myself opening up truly and I actually ended up crying because I let stuff off my chest that I was holding back for years. It helped me find out more about the person I was playing with but also find out about myself. By far the best thing I've ever done.


It was scary. Even with close friends there were questions that had me choked up. In particular, the prompt "how do you really feel about one another" made me confront some resentment that I had been holding. It was tough but I think that it strengthened our friendship.


My friends were a little hesitant at first but once we started playing it was really fun and pretty cool getting to share the things we're going through.


Honestly? The game is amazing. Hands down the best ice breaker/personal conversation I've ever had. Coming from someone whose struggled a lot with social anxiety, this game has made a world difference when its came to opening up with partners and close friends.



If you want to get in touch, email

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.

All sales are final, but of course we will exchange your order if it comes in damaged. Just send us an email at so we can help you out. We will not accept exchanges after 30 days of your delivery date.

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

We got thousands of messages from people telling us how impactful it was. 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.

So we sat down, sifted through hundreds of questions to condense it into 99 question cards and wildcards that make meaningful conversation effortless.

We created a physical representation of the experiences we were creating. When we say carefully crafted, we mean it. You won't experience anything like it.

We might need to come out with a black box of tissues.