Alex · Author of From Anxious to Secure
68
pages
The 50 Questions
A slow conversation deck for couples who've forgotten how to ask.
A 68-page PDF book. 50 questions organized into five themed sets — who you were, what you carry, the two of you, closeness, the years ahead. Plus ten lighter ones for the nights when the deep ones feel like too much.
$29
$89
One-time. Instant PDF.
Read on any device. 30-day refund if it doesn't land.
2,400+
couples
4.9 / 5
average rating
68
pages
$29
$89
one-time price
The moment this was written for.
It was 7:42 PM on a Wednesday in October and I had overcooked the salmon, again. I knew it before she tasted it. I knew it the way you know any small failure in your own kitchen — by the smell, the resistance in the fish when I lifted it off the pan, the way the lemon I'd squeezed over it had already gone tacky and dark at the edges. I plated it anyway. I put rice next to it. I put the green beans next to that. I carried both plates to the table and I sat down across from her and I said here you go in the slightly bright voice I save for when something I made is not what I hoped it would be.
She said thanks, babe.
She picked up her fork.
Both of our phones were on the table, face down. Mine lit up — a reminder about a dentist appointment. I flipped it over to check. I flipped it back. Then she flipped hers to check. Then I flipped mine, because I'd flipped hers and the rule we had never actually agreed on but somehow followed was that we got to check in pairs.
How was your day, I said.
Fine, she said. How was yours.
Fine.
The dog sighed.
We ate.
The salmon was dry. The rice was fine. I picked up my fork and I had a thought I hated.
“I don't know this person anymore.”
Not in a poetic way. I just genuinely did not know what was in her head. I hadn't asked. She hadn't offered. We had been like that for a long time. I had been married to a woman whose hand on the dog's ear I could draw from memory, and I did not know what she was thinking, and I had not noticed when I stopped knowing, and I could not point to the day it ended.
That night I started writing this book.
What the research says
“Most couples spend less than 17 minutes a day in meaningful conversation. Dr. John Gottman's research shows that couples who share six hours of genuine connection per week have dramatically lower divorce rates.”
Based on research by Dr. John Gottman, The Gottman Institute.
Seventeen minutes. That's not a crisis. That's a Wednesday.
This book is a Wednesday intervention.
Simple to start.
How it works.
Download in 2 minutes.
Complete Stripe checkout. The PDF arrives in your email immediately. No login, no app. Works on iPad, iPhone, Kindle, any browser.
Pick a night this week.
Tell him you have something you want to try. Pour two drinks. Put your phones in a drawer. Open to Set One, Question One.
One set at a time.
Each set takes about 60 minutes. One per week over five weeks. Or one per month. Or all at once if that’s who you are.
Is this for you?
This book is for you if:
- —You’ve been together one to ten years and the “how was your day, fine” loop has become the only conversation you have.
- —You love him. You’re not leaving. You just want to remember why you said yes.
- —You’ve thought about couples therapy and quietly closed the tab when you saw the price.
- —You want a structured way to start the conversation neither of you knows how to start.
- —You want this for yourself — not for him to fix something.
This book is NOT for you if:
- ×You’re in active crisis (affair disclosed in the last 90 days, abuse, addiction in the home) — please see a therapist first.
- ×You want a quick fix or a checklist that “saves” the relationship in 30 days.
- ×You’re looking for someone to tell you to leave, or to stay.
- ×You want peer-reviewed citations and clinical frameworks — that’s not what this is.
If you're not sure which list you're on — you're probably on the first one. The second list is for people who don't have to wonder.
The Details
What's inside the 68 pages.
Five themed sets of ten, plus ten lighter ones, plus reflection pages so the conversation lives somewhere after you have it.
Who You Were Before Us
Ten questions to meet the kid he came from.
“What’s the hardest thing your family asked you to carry that you never talked about?”
“Which version of yourself are you most ashamed of?”
“What was the moment you knew you were no longer who you’d been raised to be?”
+ 7 more questions in this set.
Sample — Question 14
“What's the closest you've ever come to leaving — really leaving — and what stopped you?”
Follow-up prompts included in the book:
- — What was happening that month?
- — Have you told me before? If not, why?
- — What would have changed if you had?
Every question in the book is that direct. Every question has follow-up prompts like these.
Tonight or this weekend.
You're going to put your phones in a drawer. You're going to pour two drinks or two glasses of water. You're going to sit across from him and ask question one.
Send me the PDF — $29 →Instant download. Stripe checkout. 30-day refund.
A note from Alex.
I'm not a therapist. I'm not a coach. I don't have a PhD in anything that matters here.
I'm a man who was married for four years and stopped knowing my wife somewhere around the third year and didn't notice until the salmon was dry. I wrote my first book, From Anxious to Secure, about the part of me that had been carrying the weight of the asking for years — the anxious-attached part that always reached first, always asked first, always panicked first. That book is for the part of you that doesn't know how to relax inside a relationship.
This book is what came next. After I learned to stop panic-asking, I had to learn to ask again. Differently. About the things we'd stopped touching. About the years between us. About the version of her I had married and then quietly stopped paying attention to.
I'm Alex. That's the only name you're getting. I'm protecting her privacy and mine and frankly I think the writing matters more than the bio.
These 50 questions are the ones I actually asked. The follow-up prompts are the ones I actually used when she answered with three words. The reflection pages are the ones I actually filled out, in pencil, on Wednesday nights for five months.
I hope it finds you on a Wednesday too. The salmon, the silence, all of it. It's not the end of the marriage. It's the start of the asking.
— A.
A few honest things.
Before you buy, I want to be clear about what this book is and isn't.
It is not therapy.
It cannot diagnose, treat, or replace a licensed professional. If you are in crisis, the resources page at the back of the book lists how to find a couples therapist — start there. This book is a tool that makes therapy work faster. It doesn’t replace it.
It is not magic.
Asking question 14 will not save a marriage that’s already over. It will probably tell you faster whether it’s over. Some readers have finished this book and decided to leave. Most have not. Either way, you’ll know more than you did before you asked.
It is not a checklist.
There is no scoring. There are no right answers. You will not “finish” the book in the sense of being done with your marriage. The book is a practice. The first 50 questions are the start of an asking habit you’ll do for the next 40 years if you’re lucky.
It is not for him to fix.
If you came here looking for a workbook that makes him into a different husband, please close this page and ask for a refund of your time. This book is for you. The change in him is a side effect, sometimes. The change in you is the point.
What readers said.
From real readers.
Couples 1 to 22 years in.
356+
verified reviews
“We have been in therapy on and off for two years. Our therapist costs $175 a session and we can afford one a month. This book is what we do on the other weeks. I think it's the reason the monthly session actually works now — we come in with something to say.”
— Dana K.
Married 9 years, mother of two
“We did the first set on a Sunday morning with coffee. By question seven I realized I’d never asked him this. By question ten he was crying. I have not stopped thinking about his answer to four.”
— Marissa T.
Married 6 years
“I bought this for myself and gave one to my best friend and she used it on her third date. They moved in together six months later. So either it works or we got lucky twice.”
— Jen
Married 4 years
“I’m a therapist and I have been quietly recommending this to clients who can’t afford weekly sessions. It is what I would write if I had time to write a book.”
— R.
LMFT (name withheld)
“We’ve been married 14 years and I thought I knew everything about him. Question 8 in Set One — I had no idea. We talked until 2 AM. First time in years.”
— Claire B.
Married 14 years
“My husband was skeptical. He rolled his eyes when I pulled it out. He answered question 3 for 20 minutes straight. He’s now the one who suggests we do the next set.”
— Priya M.
Married 7 years
“Simple, honest, and the best $29 I’ve spent on our marriage. We’ve done all five sets. We’re starting again from Set One because I want to hear his answers now, two years later.”
— Sarah W.
Married 11 years
“I bought this after a really hard month. I didn’t even tell him I bought it. I just left it on the kitchen table. He picked it up, read the back, and said ‘when are we starting?’ That was enough.”
— Nadia L.
Together 3 years
“Set Four was harder than I expected. We had to stop twice. But stopping was its own conversation. We’ve never been more honest with each other.”
— Teresa G.
Married 8 years
“I used Set Two on my own, just journaling the answers myself. It showed me how much I’d been hiding from even myself. Bought it for the marriage, used it on myself too.”
— Anon.
Married 5 years
“We’re engaged and did Set Five first. Now I know exactly who I’m marrying. No anxiety about the future — just excitement. This book did that.”
— Lily H.
Engaged, together 2 years
“The light questions in the last section are deceptively deep. We laughed more in one evening than we had in months. That matters.”
— James & Ruth
Married 18 years
“Read the first page and immediately forwarded it to my sister. She bought it the same day. We both did Set One the same weekend and texted about it for a week.”
— Olivia R.
Married 2 years
“The follow-up prompts are what make this different from every other card deck I’ve tried. When he goes quiet after a question, I know exactly where to go next.”
— Maya S.
Married 9 years
“I was going to get divorce papers. I bought this instead as a last try. We’re still married. I’m not saying the book saved us — but it started the conversation that did.”
— Anonymous
Married 12 years
“I keep the reflection pages in a folder. I read them sometimes when things feel hard. It reminds me that we’ve been deeper than this before and found our way.”
— Camille F.
Married 6 years
“My partner is not a feelings person. He answered question 7 in Set Two with more vulnerability than I’ve ever seen from him. I didn’t say anything. I just listened. It was enough.”
— Hannah K.
Together 5 years
“Couples therapy was $220 a session. We couldn’t keep it up. This book is not therapy — Alex is clear about that — but it does something therapy hadn’t done yet: it made us curious about each other again.”
— Tom & Sandra
Married 10 years
“Bought it on a Tuesday night at 11 PM, downloaded it immediately, and read the introduction alone before he woke up. I cried. Just from the introduction. Worth every cent.”
— Rachel D.
Married 3 years
“We do one question at dinner every Sunday now. Just one. It’s become the best part of our week. I didn’t expect a PDF to change Sunday evenings but here we are.”
— Marcus & Jo
Married 7 years
“Set Three, question 6. Neither of us could finish our sentence. We just sat there. Then she reached across the table. No words. That’s the whole book in one moment.”
— Daniel W.
Married 4 years
“I gifted this to four couples at our wedding. Every single one of them has texted me to say thank you. The best wedding gift I’ve ever given, including the expensive ones.”
— Leila A.
Married 1 year
“The writing alone is worth the price. I’ve bought self-help books that cost four times as much and none of them were written like this. Honest, quiet, real.”
— Sophie T.
Together 6 years
356 reviews. 4.9 average. The other 0.1 got their refund. No hard feelings.
The math.
Your other options.
Couples therapy.
- —$75–$200 per session
- —One hour per week
- —Six-month wait for a good therapist
- —40% of people who need it never go because of cost
- —Best when both of you can fully show up
The 50 Questions.
- —$29 once
- —60 minutes per date night, your schedule
- —Available in the next two minutes
- —Designed for the night you’d normally not have the conversation
- —Best when both of you are tired and one of you has to start
Both are good. Most of us pick neither. This is the door we built for the people in between.
Or get both books.
From Anxious to Secure is the work that comes before The 50 Questions is possible. The protocol for the part of you that has been carrying the weight of the asking for years. Some readers buy them together because the second book is harder to use without the first.
Save $9. Both delivered instantly as PDFs.
Start tonight.
You don't need to fix anything. You just need to ask one thing. The kind of thing you stopped asking somewhere around the third year, when the answers started to feel obvious and you stopped checking whether they still were.
Send me the PDF — $29 →Common questions.
Questions you might have.
Is this a PDF or a physical book?
How long does it take to do all 50?
My partner will think this is weird. What do I do?
Can I use this if we’re dating, not married?
What if it makes things worse?
We’ve tried couples therapy and it didn’t work. Will this?
Is there a refund?
Will there be more books?
The 30-day guarantee.
No questions asked.
If you finish the book and it didn't land, email me with your order number. I'll refund you within 24 hours. No form. No survey. No “what didn't you like.”
I want this book in the hands of the people it's for. If that's not you, the $29 stays with you. That's a fair trade.
— Alex
Send me the PDF — $29 →Instant PDF. Stripe checkout. 30-day refund.
One more time, the same ask.
The phones go in the drawer. You pour the two drinks. You sit across from him.
You open the book to question one. That's the whole thing. The rest of the book is just keeping you company while you do it.
Send me the PDF — $29 →Or get the bundle with From Anxious to Secure for $49. Either way, instant download. 30-day refund.
Made by Alex. No therapy promised. No marriage saved. Just a slower conversation.