What Happened!? Vol. 2

A guy I went on 2 dates with explains how and why we made the transition to friendship

This week I bring you the latest installment of “What Happened!?”, a recurring series where I convince men I’ve gone out with to sit down for a recorded interview with me and explain some mystifying element of our dynamic to my satisfaction.

I. An unusual friendship

When I am feeling unsettled about my dating life, there are a few people I am most likely to seek out to process it: my therapist, my mom, my best friend from college, my closest single friends who live in NYC, and sometimes, a guy I went on two dates with two years ago.

My friendship with this guy is strange. Strange not because of any complicated feelings or tension in the relationship, but for the lack of any obvious reason for the friendship to exist in the first place.

Music Man, a name derived from the organ music he once sent me, is someone I met on Hinge. We went on a first date for drinks where I questioned aloud whether he was interested in me. And a second for dinner where we parted with such a perfunctory, dispassionate kiss I had to actually suppress laughter. Within a day, we were both in agreement over text that we should just be friends.

By my own norms, this is the point at which our relationship should have begun to wither. It’s not that I am in any way opposed to friendship with men I’ve dated; I actually am friends with a lot of men I met on Hinge. But it is my experience that unless we have already invested a significant amount of time and emotional energy into our relationship to begin with, then other social obligations and new dates will inevitably zap us of the time and energy needed to sustain a new relationship. Maybe we’ll check in on each other a few times or suggest finding a time to meet up “soon.” But gradually the memory of him will degrade until I can no longer recall his name without looking at the list I keep in my notes app of every person I’ve ever dated.

For some reason, Music Man and I defied that pattern. Two years on and I still confide in him about my dating life and my doubts and frustrations, and he reciprocates with his own stories and insights. Every once in a while we catch up over a drink or co-work at a cafe. It is a gentle friendship, where many months can pass without correspondence or thought. But when I do eventually reach back out, I trust that he will respond with warmth and enthusiasm.

When he mentioned recently that he was performing at an upcoming music event, I bought a ticket with little thought. In the audience, looking around at all the other people who were there, I realized for the first time that I had crossed the threshold from stranger he was getting to know to friend. I wasn’t there because I owed him or wanted something from him. I wasn’t even there because I thought it would be an especially good show (lol sorry, Music Man!). I was there because it felt like an easy way to express my appreciation for our friendship. I just had one question: How the heck had it happened?

II. The Interview: Part 1 - The Why

A few weeks ago, I decided to put the question to Music Man himself.

Because he is a friend and someone I have an easy intimacy with, I went into our conversation expecting it to be straightforward and not particularly emotionally taxing.

We met at an Italian pastry shop in his neighborhood, peeled off our winter layers, and caught up about the latest updates in our dating lives between sips of mint tea. Just as I was about to transition to the interview portion of our hang, two of his friends walked in and beamed at us in a way I have come to recognize is the eagerness one is only greeted with when people think they have spotted you on a date. As soon as they were out of earshot, Music Man pointed out the irony of the encounter: not only were we not on a date, we were about to embark on a formal analysis of precisely why we had stopped dating. It was around then that the awkwardness of what I was wading into began to sink in. Music Man seemed more prepared for the conversation than I was.

The first thing I wanted to pin down was the why: Why had he wanted to be friends with me, despite our lack of romantic spark? I had some assumptions about this — that our conversations had felt effortless, that he enjoyed my curiosity, that we felt relaxed and like ourselves around each other. Music Man said all of that, in his own words, with little prompting or direction from me. But those answers didn’t address the other critical part of the question: If all those things were working, why hadn’t he wanted to date me?

I steered the conversation toward our incredibly passionless kiss at the end of our second date. What had happened there?¹

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Music Man: God how embarrassing.

Me: (laughs)

Music Man: I mean I think I genuinely was just like very confused. And, in the moment, I don't really feel like I knew what I wanted or how I felt. You know, there was a real part of me that was like this is a person I’m interested in. And I think I was just kind of unsure and, in the moment I was like, maybe this is — (he trails off)

Me: Maybe it’ll be good?

Music Man: Yeah, like, let's see what happens. But I also remember this feeling of wow that was so not romantic. Like, what just happened?!

Me: Do you think [the kiss] clarified things for you?

Music Man: No. Not really. I mean I think maybe I was hoping it would clarify things, but I don't think it did.

Me: The feeling you describe [after our first two dates] is more like some excitement and a lot of uncertainty. At what point did the uncertainty become clarity that like: no, I don't want to go on another date?

Music Man: Like probably the next morning.

Me: And what was it?

Music Man: Yeah, I think there was just that feeling of like, I was having to think too hard about things. And it wasn't just kind of effortless in the way that you imagine a romantic thing happening, you know?

Me: Do you have any sense now about — like I mean there's so much distance from it, you don't remember exactly what your feelings were — but you know me better. Do you have any more clarity now on like: “oh yeah, there's these broad categories of ways in which you're unlike what I need?”

Music Man: (long pause) I feel very unequipped to speak to that, to be honest.

Me: Because that's not the way you think or… like you're not analytical in that way?

Music Man: No, I'm definitely analytical in that way. But I feel like … there’s so many things about someone's personality that are really kind of hard to capture. Like, just the aura and essence of a person that you might be drawn to, it’s hard for me to articulate that most of the time.

I feel like in most of the big obvious checkboxy things, you were like hitting the marks. I think that in part that's why I like wanted to see you again. I mean, obviously we had like easy good conversation, but I also was like: oh this person, they're like, curious about life. I know that they're like fun to talk to. And, you know, we had like, enough overlap, right? But, yeah… I don't know… Does that satisfy you?

Me: (laughs) Well … No.

Music Man: (laughs) Obviously not.

Me: (pause) Um…. is the thing that you have some ideas [about why I wasn’t the right fit], but you're like, "I don't want to share them because that's cruel." Or is it like, "No, I really don’t have -- like anything I can tell you I don't really believe”?

Music Man: No, like I don't really feel like I have -- there's nothing that I want to say that I'm like holding back from saying because I'm worried about offending you or anything. Genuinely.

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I was hitting a wall. There was no satisfying reason Music Man could give for why he had liked me enough to want to be friends, but not enough to want to date me.

I pushed on hoping that if we identified the moment we first proposed friendship to each other, we might get somewhere.

Unfortunately, my text chain didn’t go back far enough to relive the exchange, but Music Man was pretty sure he remembered what happened. In his recollection, friendship had been his idea. When he had texted to say he didn’t want to go out again, he had probably suggested friendship at the same time. I imagined some variation on the classic: Enjoyed tonight but getting more of a friend vibe!

Hmm I wondered, was it possible that was just something he said to everyone at the time? Maybe intended as a way to soften the blow of telling others he wasn’t that into them. No, he insisted. He definitely didn’t say it to everyone. Instead, he suspected that the timing of our meeting - specifically the fact that we were both newly single - made a friendship between us more viable.

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Music Man: I think when I met you, I'd realized that this is a potential outcome. Like, it's not this binary like, we're going to date or not date. You know, there's a spectrum of like, relationships that we could have, even though, you know, the app is marketed towards romance and dating . But the other contextual bit that I think is super relevant was like I was pretty fresh out of a relationship.

Me: Yeah. How fresh, do you remember?

Music Man: It was like five months maybe.

Me: Okay.

Music Man: But, you know, it was like an almost four year relationship. Like the most significant relationship I've had. And so I think that that is a factor for sure. Like, I don't have that many recent Hinge friends, but like in that first year, there's a couple and I have to imagine maybe that has something to do with like the recency of the relationship and maybe that just like affected how I came off or maybe I just wasn't ready to — yeah, I don't know how to say it.

Me: What I'm getting is maybe you weren't ready to date, so maybe you reverted more to friendship earlier on? But the other thing is, maybe you were more open to connection. Like maybe you were more hungry for any sort of feeling of commonality and support…

Music Man: Yes. Yeah.

Me: …in a way that maybe you don't need anymore. You're like, "oh no. I'm so much stronger and further away from that painful period of transition in my life."

Music Man: Yeah, maybe I was just, like, lonelier and sadder, and needed more female friends. (laughs)

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I had forgotten this part. Or maybe I hadn’t forgotten it, but I had lost touch with the significance of it. Music Man was something like the 10th person I went out with after getting out of my own three year relationship. It wasn’t just that we were on a similar timeline of getting back into dating; it was that we shared the grief and uncertainty of exiting a long-term relationship at precisely the time that many of our friends were entering into one.

On some level, I was feeling alienated from all the people I was going out with who had been single for years. In fact, on some level, I think I felt peerless even among friends. At 28, there was almost no one I knew that had broken up with someone after such a long time together. Actually, there was almost no one I knew who had been in a relationship that long, period!

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Music Man: I remember feeling anxious about that. Like going on dates, I was like, nobody's going to want to engage with me because I'm like out of this serious relationship, and it was kind of recent. And I remember just feeling a bit of pause around revealing that — also, you know, you don't really want to talk about your ex on a date — but it came up on our date. And then when you had mentioned your similar experience, that made it easier.

Me: (long pause) I also think I had this soft spot for people at the time — in a way that I don't feel as much anymore — but you know, I felt so much guilt about breaking up with my ex-boyfriend at the time, that like other men who had been broken up with recently — you know, in a long term relationship with someone who clearly really loved them and had had a hard decision to make —

Music Man: Yeah.

Me: It made me feel in some way like: oh I hope someone is taking care of my ex-boyfriend.

Music Man: Oh yeah? (laughs)

Me: Somehow like this gesture of like —

Music Man: That's so funny.

Me: — contributing to the universe. Like, I’ll take care of this one in some way.

III. The Interview Part 2: The How?

The other big outstanding mystery in the friendship was how we had actually followed through in pulling it off.

Now if I am being totally honest, I was interested in this not solely for practical reasons. I was interested in it because it gets at a regressive theory about friendships between straight men and women that a part of me believes.

That theory (which is only the teeniest bit more nuanced than Nora Ephron’s writing in When Harry Met Sally) is that yes of course straight men and women can be friends with each other without either party wanting the relationship to be anything other than platonic. But! In order to establish that friendship, one party must invest an above average level of energy - energy that usually stems from attraction. In other words, part of what spurs a straight man and woman to hang out is that at least one of them is not entirely closed to the possibility of liking the other as more than a friend.

With Music Man, part of what fascinated me is that it seemed like neither of us took actions that were motivated by attraction. So one of the questions in the back of my mind was: who had been the main instigator of the friendship?

We had competing memories.

For me, many of the exchanges I remembered in detail were ones where he had put in the most effort. There was the time we worked together in a coffee shop, the most recent time we got drinks and then of course the time he had consoled me when I was feeling upset about dating. Maybe 6 months after we had agreed to be friends, I reached out seeking advice and he not only offered helpful perspective, but he also invited me to join him at a bbq that night. A bbq which, even though I couldn’t make it, stuck with me for being such a meaningful gesture.

He, on the other hand, remembered my efforts. He recalled me inviting him to two parties very early on in our friendship, and feeling bad about not being able to attend them. He also remembered an important early turning point for us: I reached out to him for help with a job application. A few weeks after we agreed to be friends, I made it to the interview stage for a job I was excited about. I was furiously trying to collect story ideas, and Music Man was one person I turned to for suggestions. It was a perfect exchange, he pointed out. I needed help, and he could offer me something. Plus, it was totally unromantic and required practically zero emotional vulnerability on either of our parts.

The one thing we both agreed on was that he had been the one to initially suggest a friendship.

IV. Plot Twist

But then, as I was getting ready to publish this, something funny happened. I realized I needed a photo to share and asked Music Man to go back to that very distant rejection/ friendship text and take a screenshot. And guess what? We were both wrong!

There was no mention of friendship in the rejection text! (Though please note the 7:10AM timestamp and the fact that he seemingly jammed in every effusive word he could come up with into about 3 sentences.)

Instead, the first mention of friendship came later. And what do you know… it came from me.

Remember, these are screenshots he took. So I am the black bubbles and he is the blue.

I was the one who made the first move. I was the one that followed right up with an invite to a party.

This whole time that I was searching for clues, was the answer right there? Could it really be that obvious? Was I the one driving everything? Had I just subconsciously liked him the entire time?

Maybe what makes the friendship work is that neither of us sees it as the result of one particular person’s actions. Maybe it is that (at least prior to this interview) we never subjected our relationship to a tremendous amount of scrutiny. In fact, we didn’t overthink our interactions at all.

It matters that Music Man never interpreted my initial outreach as a sneaky or desperate attempt to keep seeing him until he changed his mind about our romantic compatibility. It matters that I didn’t interpret his lack of romantic interest as a lack of care, or the fact that he didn’t show up to either of the first two (two!) parties I invited him to, as rejection.

Of course it takes both parties putting in energy to make a friendship work. But it takes so much more than that. Friendship requires resisting oversimplification - resisting the urge to see connection through a singular lens - and instead embracing the other person in all their complexity and contradictions.

As Music Man put it to me, “I kind of like ambiguous feelings.”

1. All of the transcripts that follow are exact with light editing solely for clarity. In almost every case of editing, I have removed an incomplete phrase before one us re-started a thought or deleted a filler “like.”