Can I date again?
On gremlins, data points, and learning to walk my own talk
I know I can do anything I set my mind to. I even have a sticky note in my desk that says so.
But the honest answer? I don’t know.
And for someone who coaches founders through uncertainty for a living, sitting with I don’t know is harder than it sounds.
Here’s what’s been happening.
I went on a first date. A real one. The kind I hadn’t been on in a while. And I got excited: genuinely, properly excited. By the end of it I was already making plans in my head. You know the feeling. That little spark and suddenly your brain is three steps ahead of you.
And then my gremlins arrived: those little voices that know exactly where to find you.
What if you lose yourself again? I did it once, in a marriage I thought was working. The truth is, by the end, I was miserable. I just didn’t let myself see it. What if you can’t trust yourself to see it coming this time?
And then this one, the quieter one: what if you don’t know him well enough? Every serious relationship I’ve ever had started as a friendship. My ex-husband was my roommate before he was anything else. We were friends for years before anything shifted. There’s something about walking into a room with a stranger and trying to build something from scratch that just... doesn’t compute for me yet. Like I’m missing a layer I don’t know how to get any other way than time.
So I did what I do when I’m scared. I started overanalyzing. Every message. Every word choice. Every small action became a data point for a case I was building against myself — or against him, I’m not even sure. I put red flags where there may have been none. I talked myself out of something before it had a chance to be anything.
And I showed up to the second date as a completely different person.
Stressed. Guarded. Carrying things in my head that had nothing to do with him. He noticed. Of course he noticed. He said, gently, that he felt like he’d met two different people.
He wasn’t wrong.
The thing is, very little of it had to do with him. It was about me trying too hard, against my own nature, against my own pace. I went from zero to all-in somewhere between date one and date two, and the gremlins caught up with me.
I do this in other areas of my life too. Maybe you do as well. That push-pull between I want this and what if this ruins everything and instead of sitting with the tension, we either charge forward or we shut down completely.
I shut down.
And then I spent a Sunday just following my own flow. No agenda, no plans, no optimizing. Just me and my needs and whatever the day brought. It was one of the best days I’ve had in a long time. A reminder that I am actually okay on my own. More than okay.
Which is, I think, the thing I need to keep doubling down on.
I get to be me. To dress up when I want to, because it makes me feel good, not for anyone else. To treat myself to nice things because I want them and they make me happy. To celebrate the little wins. To just enjoy life. Because let’s be honest, I am really happy. And I am very grateful. That’s not nothing. That’s actually everything.
Here’s what I keep telling my clients — and what I’m learning, slowly, to apply to myself:
Be gentle with yourself. I say this all the time. I believe it for every founder I sit with. And yet I was holding myself to a standard I would never hold anyone else to. Catching yourself not walking your own talk isn’t a failure. It’s actually the work.
Use the blank slate. In dating, it means letting each date be just a data point, not a verdict, not a preview of the next five years. But this is true for so many things in life. When you go through a separation, a burnout, a big transition, you can forget what you actually like doing alone. What your own rhythm feels like. The blank slate isn’t emptiness, it’s permission to rediscover. Go step by step. You'll find your way back to yourself. There's no rush.
My pace. My business, my kids, my friends, my life. They're not obstacles to finding love. They're my anchors. And right now, that's exactly what I need.
Celebrate the small wins. I went on a third date. On my birthday, of all days. And instead of pretending the second date hadn't happened, we actually talked about it. About the two different people he'd met, about the fact that I was feeling a little lost and knew I still had work to do on myself. That conversation? That's the win. Not the spark, not the outcome. The fact that I showed up honestly. That counts. The awkward date counts. The hard conversation counts. That's data. That's courage. That's the mountain you're climbing — and the climb itself is the good part.
I’m not done figuring this out. I don’t think I’m supposed to be yet.
But I’m sharing it because I suspect some of you are somewhere in this too. Not necessarily about dating, but about some version of I know better, so why do I keep doing this to myself?
The answer, I think, is grace. The same grace you’d offer anyone else who was learning something hard and doing their best.
Be open to what comes. But go slowly. You don’t have to be all in every time something promising shows up.
Love this Chloe!
How beautifully written Chloe!