What Happened!? Vol.1

A guy I had a huge crush on explains, in his own words, why it didn't work out

Illustration by the soon-to-be-in-Japan Nicholas Konrad.

Quick housekeeping before jumping into today’s newsletter.

First, if you’re reading this and you don’t already subscribe, please do. It’s free! And it makes me enormously happy to know who is reading! Some people have expressed concern that I’d find it weird that they were keeping tabs on my dating life. Let me assure you, it’s not. It’s weird that I have chosen to document my dating life so publicly. It’s definitely not weird that you’re curious about it.

Second, this is the first in a series I hope to continue. If you have thoughts on how to evolve the form or questions that you think I should answer in a future newsletter about my experiment of interviewing my former dates, send em my way.

Ok, here we go.

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I. The Mystery

Over the past two years, there have been exactly 3 times that I lost my shit over a guy.  The most recent one was last spring.

Here’s the cliff notes. 

I met him on Hinge, where we’d had unusually good banter. There was one anecdote on his profile that piqued my interest: He’d paddled the entire length of the Hudson River, all 300 something miles, in an inflatable canoe. I asked him a bunch of questions about it, so he sent me a 20 minute documentary he made, which introduced me to his friends, his parents, and what he looked like sitting by a fire. The effect was that, by the time we met in person, I felt like we already knew each other. 

On our first date, which was supposed to be for coffee, we ended up also getting lunch, going for a long walk, sitting on a bench on the Brooklyn Promenade for 30 minutes, and then meeting up with one of my friends. The next morning, I woke up to a message from him. “It felt really easy being around you.”

On our second date at a Mexican restaurant in Dumbo, we were so engrossed in conversation that neither of us noticed the restaurant had cleared out, until the staff started mopping the floor. He walked me back to my apartment where we eventually sat on my bed and kissed with such tenderness I was transported back to high school. With my bedroom door open like I was satisfying a request from my parents, he held my hand, touched my collarbone, and noted the different hues in my hair.

When he took a trip for work before our third date, he sent me photos, and gave me updates every day. He told me he missed my red sweater, and considered moving up his flight so we could have more time together before I headed out of town for a wedding. 

The day he got back, I went over to his apartment after work. I couldn’t get there until 9 pm, but he waited until my arrival to eat dinner anyway. Over slices of pizza, he opened up about his professional fears, his struggle with depression, and the pressure he felt to run a good time at the Boston Marathon in a few days. We made another plan to see each other as soon as we were both back. 

All of this is to say, at this point, everything seemed to be going well. I had a rare crush! Even rarer, it was a reciprocated crush! 

I sent him a message the night before the marathon:  “Good luck tomorrow! Even if somehow you are not as fast as you would like - your mom will probably still love you and there’s a decent chance I will still think you’re very cute.” 

I woke up eager to read his response, but there was nothing. 

I didn’t hear from him the next day or the one after that. What the fuck! 

II. Losing It

In those days of silence and the weeks of uncertainty that followed, I went looking for clues.

I sent screen shots of our text chain to every straight man in my life, wondering if somehow a male perspective would shake loose some meaning I was overlooking.

I asked a colleague to let me use her Instagram account to watch his Instagram stories. (Evidently too embarrassed to let him know I was doing this, but not embarrassed enough to make this request of my colleague.)

I looked at his old tweets and refreshed his personal website multiple times a day, sometimes multiple times an hour. 

I googled his name + “obituary” and “did any one die at the Boston Marathon 2024?” (No). 

I spoke on such incessant loops about it with my friends in San Francisco, who I was staying with at the time, that they started setting a timer to denote when it was time for me to move on to a different topic.

Someone more evolved than me might have arrived on their own at some kind of closure. Internalized something to the effect of:  it doesn’t matter why he isn’t texting back, the only thing that matters is that this is not how I want to feel or be treated.

But my brain doesn’t work like that. My brain is a TV with a broken controller. A few times a year, it gets stuck on a channel that is so loud, I cannot eat or think or work or sleep. The only thing that will allow me to lower the volume or change the channel is the answer to the question: what happened?

II. The Interview

A few weeks ago I sat down with Marathon Man for a 1 hour, 42 minute and 25 second interview to get to the bottom of it. I set up my phone to record (with his permission obviously),  read him his Miranda rights (if I asked anything that was too personal, he could of course just let me know and we’d move on), unfurled my legal notepad and began the questioning.

Now by this point, I should say he had eventually responded to my text. After four excruciating days, he apologized for not reaching out sooner, told me he must have missed my message and admitted to having had a terrible time at the marathon and feeling quite despondent in the aftermath. We even went on another date or two after that, but it was no use. 

In retrospect it is obvious to me that something in our dynamic shifted at precisely the time I sent that good luck message. Whereas once there had been two people pumping energy and urgency into our budding relationship, now there was just one. We agreed to just be friends.  

At the time of this interview we had been friends for about 3 months, which mostly meant that we were occasionally DMing each other on Instagram about our respective creative projects, and making earnest but low-effort attempts to grab dinner or go for a walk. He gave me a hug when he met me, we did some brief catching up and then I laid out my vision for the interview. 

My goal was to get him to recount his feelings toward me at every step of the way of getting to know me, and compare that to my own feelings.  He should not hold back; he was not going to hurt my feelings. I wanted the truth. 

III. Here’s what I learned. 

First, if you date someone kind and good humored, it turns out they are basically incapable of delivering criticism to your face, without immediately following up with a caveat or a compliment or a self-deferential joke. As a service to you, the reader, I have tried to mostly cut out the stuff about how great I am. (But so that you do not sour on this very nice anonymous man, just know that getting him to admit anything even remotely disparaging took all of my journalistic effort.)  

So to begin…how did he feel after our first date? (All bolded text is verbatim - as I said, I recorded and made an exact transcript.)

Him: I knew that I liked you enough to want to hang out again and was excited to figure out when that was going to be.

Me: Yeah, but relative to other dates? 

Him: I don’t think on that first date I was thinking… I was not imagining our whole life.

Me: Yeah, ok. So that to me sounds like an average level of interest for you.

Him: No. I mean, average is: go on a first date and it's like, all right, that was cool, I'm glad I met that person, but I don't really need to hang out with them again.

Me: Okay, so above average?

Him: Definitely.

When it came to our second date, he recalled a few… shall we say… faux pas (?) on my part. 

First, that the restaurant I chose seemed “really random.” (We live in the same neighborhood, where there are tons of good spots. But I had chosen a place that was a few neighborhoods over and required us to walk for 30 minutes. Which side note: I’m gonna throw my therapist under the bus here and say that she actually helped me come up with this plan. It was supposed to help him relax. Apparently this was not effective! )

And then second, that on our walk back to my apartment, “you were talking a lot about weird past dates. You said you don’t usually kiss on the first date, or second date even. And I’m somebody who already has terrible anxiety of how to make moves… I was like what the hell? What am I doing now?” (Side note: LOL this might have actually been worse than he conveyed or remembered. I was nervous!) 

Despite all of that, when I asked him about how he felt leaving the second date, he lingered on our kiss as a positive indication of his level of interest. 

Him: I feel like there was some part of me that was maybe into the idea of not rushing into things and going beyond just making out. I feel like um... I knew that I liked you and, I just didn't feel like— for whatever reason, I didn't need to be having sex or something like right then and there. 

Me: Yeah. Yeah, totally.

Him: But I feel like had I not liked you that much. I almost would have been more likely to have — (he trailed off)

Me: Gone for hooking up?

Him: Yeah. Which is interesting.

Me: Yeah, why is that?

Him: I think that's because my last girlfriend, we... on our second date, she said something like, I'm trying to go slower with you just to make sure this doesn't get fucked up. And it worked then. And I feel like I'm still in that mindset, I guess. 

Me: So why would you be more likely to hook up with someone you’re not too interested in?

Him: I guess I feel like maybe sex is either like a very meaningful thing to have with someone. And if I really like them, that's great. Or it could just be a really fun thing.

Me: Yeah, got it. 

Him: And I felt like, I feel like, when I'm into someone or I think that I will be into someone or I'm getting into someone, I'd rather it be a meaningful thing.

Ok. So, now for the real divergences. 

The first was that his effort to switch his flight to come back earlier, before our third date wasn’t really a signal of his level of interest. His work sends him all over the world all the time. To date anyone, he just accepts that it will require some level of moving stuff around.  That said, the extent to which I also seemed to have to move around a lot of stuff in my life to see him, registered to him as a sign of a potential problem. 

Him: There was some realization of, like, the logistics of us dating would have been pretty challenging. 

Me: Yeah. 

Him: I felt like you were very busy. Are very busy. And I'm busy, but in a different way. Which didn't you know - it didn't bother me, that’s like not like the reason [our relationship didn’t work out], probably. But there's like some aspect of, like, this would be an interesting way to be hanging out with someone.

The second divergence was that where I interpreted our nervous energy as a positive sign of infatuation-fueled jitteriness, he interpreted it as a sign that something about our dynamic wasn’t working.

Him: It felt like -- 

Me: I was definitely nervous.

Him: You were nervous. And it just felt like slightly uncomfortable.

Me: Yeah. 

Him: The ease, the ease, felt lost. Like the first few times we hung out it was just like oh this is — we’re kind of just grooving.

Me: It's interesting that that could be telling to you because maybe it's more telling than I have realized… For me it’s like the ease is something that comes with time. But maybe that’s like not your experience of dating. It’s like if the ease is not there early on, that’s meaningful?

Him: Somewhat.

And then maybe an hour into our conversation, his tone shifted and he spoke with a lot of emotion about one specific moment he remembered. 

Him: I feel like on that third date too, you said something to me that I feel like is triggering. You said something along the lines of like, I can't figure you out. Or, I don't understand you.

Me: Okay. Yeah. 

Him: And, I feel like I've been told that before 'cause of I'm how I am. But I think there's part of me that, like, wants — (he takes a long pause)

Me: To be with someone who does get you?

Him: Yeah. Yeah.

Me: I see. So it was like this moment of like: hmm maybe this isn't right then?

Him: Yeah. And I don't think you — You didn't mean it in a way that was like: I don't understand you at all. 

Me: But it was telling somehow. It, like, revealed something?

Him: You were just like, I can't quite figure you out.

Me: Yeah. Did you feel like you could? Like when I said that, were you like: yeah, I maybe can't figure you out, too? Or did you feel like you could figure me out, but maybe I just couldn't reciprocate it?

Him: You're better at explaining things. I can understand why someone would say they can't figure me out.

Me: No, but I just mean in terms of that feeling of like, you want to be seen by someone else, but also you presumably want to feel like you really see your partner too.

Him: Yeah. 

Me: Was that a concern too, here? 

Him: I don't want to say that I had you figured out, but maybe enough that I wasn't worried about it. Yeah.

We went back and forth on this point about me not understanding him for quite a while. Was the thing I didn’t understand his interests - how to engage with his work and how much went into his training as a runner? Was it about the different way we processed information? That I was more verbal and analytical and he was more visual and abstract? Also, how was he so sure of this after just a handful of dates?  

Me: Maybe this is also reflective of our incompatible differences, but there's a part of my brain that works like: "You're smart. You can figure anything out.” Like, of course, if you gave me more time, I would figure it out.

Him: Yeah. I'm sure we could have kept going on dates and, like, had fun, but that feeling of doing things in the ways we'd want, I don't think that was going to work, intuitively. My last relationship was like a year long and I felt that early on.

Me: But ignored it?

Him: Ignored it. And like the worries that I had early on are the same worries that we broke up about. And I feel like that and other situations like that, it's been proved one way or the other, that it's not worth forcing it I guess.

I feel like I have had the feeling of like when you meet someone and it's like, almost upon saying hello, there’s this feeling of attraction or a connection. And those feelings just kind of stick around when it is meant to be it seems. And I didn't have that I guess.

Me: But the excitement was there for the first and second date. It just went away after the third?

Him: Yeah. 

Me: And, it felt clear it wasn't about anything that happened on the third date. It was about getting to know me better and understanding: oh this person is this way that is like just not going to work?

Him: Yeah.

Me: (long pause, then definitively) Alright!

Him: (laughing) oh that's it, done!

Me: (laughing) I feel like I got the answer. I feel like I understand and I could write about it now.

Me, in San Francisco, still waiting for Marathon Man to respond to my text and reading aloud our previous messages for the 1000th time to my friends Summer and Alex. (Thank you for putting up with me.)

If you’ve made it this far you might also enjoy this follow up letter where I offer my thoughts and feelings on the interview.