Amos 3:3
“Can two walk together, unless they are agreed?”
Before you walk together,
talk together.
99 Questions is a guided conversation deck and a companion app, built to help couples discover real alignment in faith, values, and vision before they commit.
Inside the Deck
Ninety-nine cards.
One real conversation.
Each card is hand-written to invite something deeper than a yes or no — a memory, a fear, a hope, a conviction. Pull one a night or work through a category in a weekend.
- 01 Faith
- 02 Family
- 03 Future
- 04 Fun
- · 99 hand-written questions across four categories
- · Hard-cover keepsake box
- · Quick-start instruction card
- · Companion app access via QR code
Proven over potential.
How it works
Three Simple Steps
01. Open the deck
Pick a category, or shuffle the whole stack. Light a candle, pour something warm, put your phones face-down.
02. Ask the question
One reads, the other answers. One question at a time. Let it land. The only rule is honesty.
03. Listen, share, pray
End each session with a one-line prayer over what you heard.
The Deck
Ninety-nine cards.
One real conversation.
A deck built to take two people from surface-level small talk to the things that actually shape a future. One card at a time.
Who it’s for
- Couples dating with intention
- Engaged couples ready for the real conversations
- Newlyweds building the foundation
- Pastors, mentors, and small-group leaders
- Anyone who wants depth in their dating life
- Anyone who wants God at the center
What is included for sure
- 99 thought out questions across four categories
- Faith, family, future and fun
- How to use card with instructions
- Hard cover keepsake box
- QR code for the app
The Companion App
Keep walking, even on the days you can’t sit down.
One question a day, just for the two of you. Answer privately, unlock together, and build a record of the conversations that shaped you.
- ✦ A daily question, delivered to both of you
- ✦ Private answers, unlocked together
- ✦ Scripture reading plans tied to each category
- ✦ A shared journal of every answer you’ve given
Early voices
From couples walking it out.
“We've been engaged eight months and we'd never talked about half of what's on these cards. One night with the deck was worth a month of date nights.”
“I use it with every couple I counsel now. It does the work of three sessions in an hour, because the questions don't let you hide.”
“Eleven years in and we're still finding cards we don't have an easy answer for. That's the point.”
Our Why
We built this because we needed it first.
We’re both 25. We’re not married, not yet. But we’ve spent enough time entertaining potential instead of looking for what’s proven, especially proven in someone’s walk with the Lord. To know the difference is crucial. The questions that actually matter almost never come up until they have to. Dating mostly happens in the shallow end.
We wanted to skip ahead. Not to rush anything, just to make the conversations that matter feel natural. To turn the hard questions into a Friday night on the couch.
99 Questions is our way of putting ninety-nine small invitations in your hands, one card at a time. Real questions, honest answers, and a conversation worth having.
If this deck moves one couple from small talk to substance, it did its work.
With gratitude,
Brennen & Jacob
FAQ
Honest answers.
Do we have to be Christian to use 99 Questions?
The deck is rooted in a Christian worldview and Scripture, but
the questions themselves invite anyone willing to be honest.
That said, you'll get the most out of it if at least one of
you holds, or is genuinely exploring, Christian faith.
When does the deck ship?
Pre-orders open later this year, with first shipments rolling
out shortly after. Join the waitlist to lock in launch pricing
and be the first to know.
Is the app included with the deck?
Every physical deck comes with a redemption code for the
companion app at launch. The app will also be available
separately.
Can we use this for pre-marital counseling or small groups?
Yes. That's one of the most common use cases. A facilitator
guide will be available alongside launch.
Join the waitlist
Be the first to walk it out.
One email when pre-orders open. No noise, no spam. Promise.
We'll only email you about 99 Questions launches.