Issue 01 — She Had Great Taste in Lipstick and Terrible Taste in Follow-Through

We matched on an app, which I'll get into in a future issue — the app era deserves its own series, possibly its own support group — but this one felt different from the first message. Three weeks of talking before we even met in person. Real conversation. The kind where you're laughing at your phone alone in your house and your dog looks at you like what is happening to you.

Her name was Janae. Makeup artist. Long dark hair, always done, the kind of woman who shows up to a bar after a full day on a photo shoot still looking like she stepped out of the shoot itself. She was sweet and a little witty — not as quick as she'd been over text, but charming enough in person that I didn't clock it until later. She was shorter than me, which — if you read Issue 00 you know this is not usually how it goes — so I noted it quietly and moved on. Not my problem tonight.

I'd asked her weeks earlier what her favorite drink was. Offhand, conversational, the kind of question you ask when you're trying to learn someone. I remembered. So when she walked into that bar in Studio City I already had it waiting for her.

She sat down, saw the drink, and smiled like I'd done something remarkable. I hadn't. I'd just paid attention. Apparently that's remarkable. We can unpack that another time.

We sat at the bar for maybe twenty minutes and it was easy — the kind of easy that makes you suspicious if you have trust issues, which I do, but I was choosing to grow. She told me about her day on set, I made her laugh, she made me laugh, and then she did something I was not prepared for.

She initiated.

Not me. Her.

She wanted to move to the table near the dartboard. She wanted to play darts. She came up with the game — whoever threw closest to the bullseye got to ask the other person a question, full honesty required. We went back and forth, questions flying, and then she raised the stakes. If she beat me on the next throw she got to dare me instead.

I agreed, which in retrospect was either confidence or stupidity and I'm still not sure which.

She beat me. We moved back to a corner booth, out of sight of most of the bar, and she leaned in and told me what the dare was.

She dared me to kiss her.

I did not hesitate.

I want to be clear about what happened in that moment because I need you to understand the context of everything that comes after. There were fireworks. Actual fireworks, in my head, the kind you feel behind your eyes. And here's the thing — I'm usually the one making moves. I'm usually the one reading the room, deciding the timing, hoping I got it right. This woman had been running the entire evening and I was just showing up to my own date.

It was extraordinary.

She wanted to keep going. Food, she said. Her place. She lived close enough to walk.

On the outside I was calm. Collected. Cool. On the inside I was a highlight reel and a prayer.

We ordered food to the bar and walked to her place. Took our shoes off at the door — which I respect, house rules — and I held up the bag and asked where we were eating. I was thinking drinks, maybe her couch, the conversation continuing into something easy and warm.

She grabbed the bag, put it on the dining room table, and jumped on me.

I caught her. Obviously.

She pointed down the hall. I carried her.

We landed on her bed and it was going exactly as well as you're imagining and then her phone vibrated and she said hold on.

I held on.

Ten minutes. I sat on the edge of her bed while she texted someone for ten full minutes. I want you to picture this. I want you to really let it land. The food was on the dining room table. I was on the bed. The momentum of the entire evening was somewhere in between, slowly going cold like my coffee on a Sunday morning.

She finished, put the phone down, looked at me and said where were we — and kissed me again.

And then she just. Stopped. Slowed down, pulled back, and curled into me and closed her eyes.

She'd had two drinks. I counted. I let it go.

I laid there in the dark doing the math — stay or go, stay or go — and eventually the burrito on the dining room table started feeling like the most reliable relationship in the room. Her phone went off again, she stirred, we both got up, and I told her I'd had a good time and we should do this again.

She kissed me goodnight at the door.

I called a Lyft. I ate the burrito at home, alone, and decided the evening had still been a win overall.

The next morning I texted her to plan a second date. She said yes. We picked a day, picked a place, and for the days leading up to it we kept talking — jokes, voice notes, the same easy rhythm we'd had before. I let myself think this was actually going somewhere.

The day before the date she went quiet.

I didn't think much of it. Sometimes people get busy. I know what it's like to be on set and unreachable, phone buried in a bag somewhere between takes. I gave her the benefit of the doubt because I always give people the benefit of the doubt, which is a thing I am actively working on and also will probably never stop doing.

Morning of the date I texted her. Good morning. See you tonight.

Nothing.

I watched my phone the way you watch a door you're not sure anyone's coming through. I went back and forth all day — show up or don't, show up or don't. The hopeless romantic in me, the one who had her drink ready before she walked in, the one who caught her at the door and carried her down the hall, that part of me said: she's on set. She's busy. She wouldn't just not show up.

Two hours before I texted again. See you at 8?

Still nothing.

I went home. Got ready. And I showed up.

I go to this place enough that the bartender knows me. I sat down, ordered a drink, and told him I was waiting for someone. He checked back in after a while. Asked if I wanted to order food.

I knew then.

But I stayed anyway. Ordered dinner. Had another drink. Sat at that bar by myself and ran back through the whole thing — the drink I'd had waiting, the darts, the dare, the fireworks, the ten-minute text interruption I should have paid more attention to, the burrito — looking for the moment I missed. The thing I said or didn't say. The version of events where this makes sense.

I never found it.

I never heard from Janae again. No explanation, no read receipts, no closure of any kind. Just a really good first date and then silence, the way LA gives you a perfect weather day right before it doesn't.

To this day I don't know what happened.

I've made peace with that.

Mostly.

— Alex

Next issue: an Airbnb in San Clemente, a balcony with an ocean view, two unopened canvases, and a woman stationed in San Diego who taught me the difference between someone who wants to be there and someone who's just present. It's a bigger difference than you'd think.

Nobody became a developer to write documentation. But the docs still need to get written — PRDs, README updates, architecture decisions, onboarding guides.

Wispr Flow lets you talk through it instead. Speak naturally about what the code does, how it works, and why you built it that way. Flow formats everything into clean, professional text you can paste into Notion, Confluence, or GitHub.

Used by engineering teams at OpenAI, Vercel, and Clay. 89% of messages sent with zero edits. Works system-wide on Mac, Windows, and iPhone.

Try Wispr Flow free