"I have never known somebody so deeply in such a short amount of time."

For Dating

Back in stock after 3 months of being sold out

The game that challenges you to have actually interesting conversations on your dates. The questions are sequenced to break the ice, get real, and go deeper than most dates. You end up knowing each other more deeply by turning the conversation into a game.
  • 99 questions made for someone you're into
  • 3 levels to start safe and end up somewhere honest
  • Every card opens a conversation that would never come up on its own
Jordan

"Used it on a first date last night. Shared more than I expected to. Right after, we were cuddling and kissing. Already planned date #2."

Most dates are boring interviews where you ask what everyone else did. This isn't.

You get to just be you

no scrambling for the next thing to say, no performing

Skips the small talk

you're into real conversation way faster

Not just on you to carry it

the questions do the heavy lifting for both of you

Wins either way

even with no spark, it's still a good night

Less pressure, more connection

nobody's trying to impress, so people actually click

No awkward silences

the one thing everyone's actually scared of, gone

3 levels to know them deeply

Ice Breakers

Ice Breakers

You're already talking differently than you were five minutes ago.

Confessions

Confessions

You're both surprised by what you share — and surprised it felt okay to.

Getting Deep

Getting Deep

You feel seen. They feel seen. The date you wanted.. this is it.

Challenge

Challenge

Wholesome, memorable, and the perfect landing.

We thought deeply about this game..

and the numbers show it.

100k+
customers growing deeper relationships
95%
5-star reviews from happy customers
1M+
followers in our community

Based on internal studies and customer feedback surveys.

If you're in your dating arc.. the choice is clear

Our games vs others we've seen

If you're in your dating arc.. the choice is clear

Our games vs others we've seen

For Dating
For Dating
Others
No AI-generated questions.
Every question tested with real people
Only the best made the cut — no filler
Made specifically for dating
Months of testing before release

A few things people wonder

Won't it feel forced on a date? +

It doesn't. Because you're both picking and answering together, it never feels one-sided. It feels like permission to be more authentic.

Are there dirty or uncomfortable questions? +

No dirty ones. A few flirty ones. The goal of every question is to reach a new level of comfort.

What if we've been together for a while? +

Some of the most powerful moments happen with couples who think they already know each other. The questions surface things that somehow never came up.. and suddenly you're seeing a side of them you didn't know existed.

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

What if it doesn't work for us? +

Keep the game and get a full refund. Not as a policy, but as a promise. If it doesn't open a moment you love to be in, you shouldn't have to pay for it.

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.

Are there dirty or uncomfortable questions? +

No dirty ones. A few flirty ones. The goal of every question is to reach a new level of comfort.

How can I contact support? +

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

What if it doesn't work for us? +

Keep the game and get a full refund. Not as a policy, but as a promise. If it doesn't open a moment you love to be in, you shouldn't have to pay for it.

Our guarantee

If it doesn’t bring you closer, you don’t pay for it.

Play For Dating with someone who matters to you. If you don’t walk away knowing them better, ask for a full refund within 30 days. No hassle.

  • 30 days to play it and feel it
  • Full refund not store credit
  • Under 1% of customers ask for one

Customer Reviews

Overall rating: 4.5 / 5 from 36 reviews.

I've been taking a random question a day out of the box and sending it to my best friend and we've both been answering it. We've both been taking it seriously because i as well as she want to both get to know each other more on a deeper level. It's been really nice.

For Dates

My now girlfriend and I played this on several dates and really enjoyed it, one of the cards even set off our first kiss, I’d highly recommend it.

For Dates

Played this with my wife of 2 years and we had an amazing time. It's becoming a weekly activity for us to just stay connected!

For Dates

I bought the couples and dating version, and I used the dating version last night for a first date! And honestly it was great! I learned so much about her and shared more than I thought I would be willing to, but I feel like it changed the whole dynamic of the night after! Almost right after we started cuddling and kissing 😂 but besides that, every conversation there forward was just easy, felt natural, and we even planned the next date! I would VERY HIGHLY recommend this game for anyone for a first date, as a couple, or what have you! 10/10 need more added to the cards!

For Dates

10/10 - I rarely leave feedback on things I purchase, but the story I want to share has had a significant impact on my life. I had been struggling for a couple months after being laid-off from my recent employer and lost touch with a lot of the things that gave me joy. A couple weeks ago, I spontaneously decided to walk to a local music venue for a live show and met the most interesting woman of my life. A few days later, I came across an advertisement for these cards on Instagram and never felt more compelled to make the purchase. The next time I saw her, we dove into the card game, and I have never, in my life, felt like I know somebody so deeply in such a short amount of time. I have a strong likelihood that she's the one now, and I cannot express my thankfulness to this company and the mission behind it. -Brendan (Tampa, FL)

For Dates

These questions not only broke the ice but helped push me and my girlfriend to open up to each other. We are so grateful for the prompts because there were stories shared that would not have been told otherwise!

For Dating

Love HDWYG. My boyfriend bought the first deck and I got the second . It’s been great learning more about him and being able to open up more myself. Only going to improve our relationship :)

For Dates

I played the cards with me and an old friend reconnecting after years of seperation. It was fun getting a man to talk and give long explanations of reply. Made me think how I see myself also. Love it.

For Dates

Looking forward to enjoying many , many evenings utilizing the amazing conversation starters

For Dating

Thanks for real, Stain Almost two weeks ago I sent a message letting you know I was charged withe 3 purchases, I didn't approve. I was charged for these and sent an email to the support desk but I never heard back from you? is this a scam? Why is it taking you so long to return my message to your info email? Marc Djikas 239-955-2626 m.djikas#yucatanswfl.com

For Dates

Theyre okay

For Dating

Gave it to my son as he is beginning to date.

For Dates

Customer service has been completely unresponsive for almost 3 weeks and 4 emails later.

For Dates

Love these cards. It helped me build a stronger foundation with my partner. Now I bought the lovers and sequel cards. Highly recommend!

For Dates

Overpriced. Only about 25% of the cards offer interesting questions. This is something that AI or yourself, with a little thought could write up and save a lot of money.

For Dates

My lady friend and I enjoyed it and it really helped us to break through nervousness of dating at our stage of life.

For Dates

Good variation of surface level and intimate questions; all questions were thought provoking and made the date go quite well!

For Dates

This was actually a really good game. We played the Dating one the night I got it. We are in long distance and were asked each other as many questions as possible. This gives us so many more in depth questions and we are learning alot more Deeper questions about each other. Love it!!!

For Dates

I love getting to know my partner on a different level that we normally wouldn't think to explore

For Dates

I think it's something me and my partner can always go back to since we're always changing and evolving. I dont think any answer will always be the same, Thank You!

For Dates

its great i loved it

For Dates

Probably a bit expensive for value. Marketing is way better than product. Its great for half that price. Can I return this?

For Dates

Perfect

For Dates

Im lookong forward to adding these to my couples getaway conversation starters

For Dates

Better than I expected. I love the questions!

For Dates

Good questions to help decide to continue talking with someone. Very helpful to getting to know someone you may want to talk to some more.

For Dates

Amazing way for me... Amazing way for me and my new partner to connect and get closer

For Dates

it really helped me... it really helped me create a deep connection with my date. especially with the challenges after every round!

For Dates

Love the questions

For Dates

I love love love this game! It me and my date open up so mich toneach other, to where i could understand so much about him and why he behaves the way he does. These cards are a must have. I will definitely purchase the other cards

For Dates

Quality product!

For Dates

Amazing and fun game to play. I've stayed up many nights already playing with the person I hold most dear. I could not have asked for a better way to connect with them on a way I could not normally. I've learned so much about others and myself.

For Dates

It’s fun and helps build confidence How Deep Will You Go? For Dates has been helpful both to get a conversation going and to keep it fun!!

For Dates

Very thoughtful. Recommend.

For Dates