50 First Dates

On re-entering dating after eighteen years. What I've learned. What still terrifies me.

I went on my first date in eighteen years.

I want to let that land for a second. Eighteen years. The last time I went on a first date, smartphones did not exist the way they exist now. Dating apps were not the primary mechanism. There was no algorithm deciding who you might want to spend time with based on a set of preferences you selected on a Tuesday afternoon while eating lunch.

I came back to the world of dating in my late thirties and it was like arriving at a party where everyone had been there for years and knew the rules and I was standing at the door holding the wrong kind of hostess gift.

I asked my friends how it worked. They looked at me with a specific kind of pity.

Here is what I have learned in the months since:

First: nobody teaches you this part. There is no guide for re-entering dating after a long relationship. There are books about divorce and books about grief and books about starting over, but nobody quite addresses the specific strangeness of sitting across from a stranger at a restaurant trying to figure out who you are when you're not attached to someone else.

Second: I needed rules. Not because I'm rigid, but because having a framework meant I could show up and actually be present instead of navigating everything in real time. The rules: daytime only. I drive myself. I buy my own drink before they arrive. One drink maximum. Always an activity, not just dinner. Sixty to ninety minute limit. One real question per date. No ex talk. Always debrief after.

Third: the fear I had about my body — about someone seeing me, the 38-year-old body that's been through things — was not the thing to be afraid of. The person across the table is not conducting an audit of the things you're self-conscious about. They're looking at how you laugh. Whether you seem like someone interesting to know. Whether there is something alive in you.

And here is the thing about dating at 38 that nobody warned me would be true: what I'm drawn to now has almost nothing to do with what I was drawn to at 18. At 18 it was body first, if I'm honest. At 38 it's brain first. Then heart. Then eyes — not the color, the quality, whether something alive is happening in them.

That is not a consolation prize. That is an upgrade.

I am documenting all of it. The dates. The apps. The rules. The moments that were awkward and the moments that were genuinely good and the moments that were both at the same time. I am doing this publicly and honestly because I think women deserve to see what this actually looks like — not the highlight reel, not the rom-com version, the real version.

There is something the most important thing a community can do is introduce itself to itself.

That's what the 50 First Dates series is. Come along for it. ❤️