Written by our founder, Sarah.
I’m Sarah, the founder of Strategy Journaling Co. I’m one of those people who has been journaling since I was four — if you count barely legible scribbles as a journal, which I do. Our first product, The Date Book, came straight out of my own years of online dating.
I’m also someone who genuinely loved online dating. I made a lot of friends, met a wide and strange slice of humanity, and had a good time — even with the heartbreak and the rejection and the occasional genuinely awful date. But it didn’t start out that way.
When I started dating, I made just about every mistake there is to make. On my second-ever online date, I texted my best friend that I’d found love. (I had not found love. Real love turned up seven years and a relationship or two later.) Through all of it, I kept a journal — not to cheer myself up, but to write down what actually happened on each date, and how I actually felt about it. Those turned out to be two different things more often than I’d like to admit.
How my journal became a tool
I’m a fairly calm person. My life isn’t very dramatic and my emotions rarely hit extremes. So I wasn’t prepared for what dating did to me.
There was one person who could scramble my judgment completely. We’d have these intense, whirlwind dates — full of laughter and long conversations — that felt amazing in the moment. Then, almost as fast, the doubts would creep in. I’d decide, clearly and finally, that we weren’t right for each other. And that would be that.
Except a week later, in a weak moment, I’d text him again. I’d get pulled back into that first rush, that feeling that maybe I’d been overthinking it. It was an endless loop of highs and lows, certainty and doubt, and my normally level-headed self was nowhere to be found.
It was exhausting, and honestly a little embarrassing. I’d grown up around volatile relationships and told myself I was too clear-headed to repeat them. Apparently not — here I was, losing track of my own judgment.
At first, writing about my dates was just a way to get the noise out of my head. But I kept doing it, after every date, and the writing quietly changed jobs. It stopped being a place to vent and became a record — of what happened, and what I’d felt, before my memory could tidy either one up.
And once it was a record, I could see things I couldn’t see from inside the moment. Patterns in what I did, in how I reacted. On paper, that endless loop with the judgment-scrambling guy wasn’t a mystery — it was right there, the same move over and over. I got better at saying no and meaning it, and at noticing what I kept saying yes to.
What I could finally see was that the volatility wasn’t really about any one date. It was about my own insecurities, and my habit of talking myself out of what my gut already knew.
Writing it down didn’t fix any of that by itself. What it did was hold the version of events my memory kept quietly editing — and that record made the decisions easier. The more I wrote, the less I was at the mercy of whichever feeling was loudest that day. Many dates later, that same clarity is how I recognized that Ryan — now my fiancé, met on an online date on Hinge — was different.
The Birth of The Date Book
Once journaling had done that for me, it seemed obvious that other people could use the same thing. So I went to my local bookstore to find a journal made for dating — and there wasn’t one. There were journals for astrology, for fitness, for keeping track of what you’d watched on Netflix. Nothing for dating. Which was strange, given that who you choose as a partner is one of the biggest decisions you’ll ever make.
I’d also seen up close what a bad relationship can do — people I love working their way out of ones that quietly wore them down. So I built the tool I wish I’d had: a structured place to pay attention to your dating life while you’re in it, not just after. Everything we’ve made since starts from the same belief — that the time you spend thinking honestly about your own life will teach you more than anyone else can tell you.
My Hope for You
A lot of people I know hate dating right now, and it’s true that modern dating culture has gotten warped. You’ll probably come out of it with a few stories — the person who stole your wallet, the one who picked a fight with the waiter. My hope is that The Date Book gives you a way to pay attention through all of it: the good dates, the strange ones, and the ones you only understand later. And I hope that, like me, you look back on this stretch of your life and find it was a good one — a strange, interesting time that happened before you met your person.
I’m only an email away — let me know what you think of the book at sarah@strategyjournaling.co.
All the best,
—Sarah