We were hanging out at the Museum of Reclaimed Space in Alphabet City. It was a Jane Jacobs event where we learned about community gardens and squatter's rights. A good mix of oldheads and transplants who wanted to feel cool. An oldhead asked if I was feeling ok (I was wearing a mask inside the museum). I feel fine, I said. I'm mildly immunocompromised. I've been so burned out on people's weird medical opinions since Covid that it felt like just another day. But then I saw you.

You are the kind of person who isn't immediately attractive at first glance and I mean that as a compliment. I would describe you as understated, introverted, and maybe a bit shy. Long brown hair, cute 90's sunglasses, and a curious nature. You mentioned you had gone to grad school for cybersecurity and electrical-something, so I started talking to you about the grid. I've been on a Wikipedia kick about electrical grids ever since Trump invaded Iran and AI got crazier - just super interested in the feasibility of a foreign actor hacking in. I asked you about grid decentralization and you commented on how there's an eastern and a western division, which tracked with what I read on Wikipedia. Color me impressed.

We then went into the usual conversation that happens whenever I meet someone new here – “Where did you grow up?” “How long have you been in New York”, etc. The necessary evil of getting to know new people - or more aptly, the necessary boredom. But with you it felt natural.

By now we were walking to Tompkins Square, trailing the rest of the group ever so slightly. It was sunny and you took off your jacket, and it was like a ray of light had spotlighted you in the most perfect way. In that moment, you were so beautiful to me. Maybe it was our meandering, kind conversation - or the way the sun hit your shoulders - but I felt so attracted to you. We reached the park, and the organizer was talking about the fences and how they acted as a strategy to keep out vagrants. He used the word strategy again and again - a never-ending war of attrition between the oldheads and the city. Then the organizer declared the meeting over and bid us all adieu, and I did something that felt a bit...premature.

I've been struggling a lot lately in the romance department. I'm looking for a long-term relationship with a woman I can connect with deeply. I've been told I am good-looking dude, but I also have a shyness and nondescript nature that makes it tough to stand out. I often feel lonely in New York. Or overlooked. But I still approach because nothing would happen otherwise.

I went to a singles event last Monday at McCarren where there were a bunch of index of cards on the table. The cards had "WHAT IF WE" in big bold serif font across the front and in smaller letters underneath there were a list of activities: go to a play, chill in the park, etc. On the front of the card I wrote my name with a heart next to it along with my phone number.

One of my frustrations with the folks I approach (not just women) is that I rarely see any of them again. The ones I do I end up becoming great friends with. It's like seeing someone again is the great filter that most people can't get past. The ones that do are my people. And I had a feeling you might be one of them.

I should have kept talking about our childhoods. About non-state actors. About city planners. But instead, I gave you one of the date me cards and was like, "text me if you want." I felt like I was being cool and mysterious. Like not lingering was somehow signaling to you that I had better things to do, Nothing could have been further from the truth.

I really enjoyed getting to know you. We were only strangers on a 15 minute journey, but you were one of the people I wanted to stay on the ride with. I could have been more organic. But sometimes I'm tired of organic and just want a nasty dollar slice. I've had some nice convos with people, some that would stretch over an hour. But seeing them again wasn't any easier. You know the drill. Ghosting, excuses. The great filter.

I'm very thankful for the friends I have in life. I don't have many, but they are my true compadres. I’ve been trying so hard to meet my significant other, but the filter seems to be working too well. Sometimes I wonder if I should widen it a bit to let more people through, but that usually doesn't work. They can sense I'm being a simp, inauthentic or whatever. The right people kind of just know what they are looking for – me.

You never texted me. I pretty much knew you wouldn't after I walked away. It stung for the next 24 hours, I'll admit. I've asked several people about it, people I consider to have a lot of experience interacting with strangers. They talked about energy, mirroring, and rejection. It felt good to chat with these enlightened beings, but I still feel like I messed up with you. If only I would have been more smooth, patient, flirty, intimate, or bold.

If only I wouldn't have asked you out on an index card.