My first-ever girlfriend broke up with me a few months after we started dating, over the summer after eighth grade. That summer I was at a traveling theater camp whose address changed every week, and the ensuing confusion meant that the love letter she sent me at the start of the summer got sent back to her. In the interim, she changed her mind about wanting to be with me and wrote me a second letter, this time a breakup letter. And then—and I swear this is 100% true—she sent me both letters, to the right address this time, in the same envelope.

That summer I had suspected things between us might fall apart, and even though we barely had much of a relationship to begin with, I desperately hoped what little we had wouldn’t come to an end. In middle school I saw people as cleanly divided between those who had entered the World of Girls and those who hadn’t, and until this girlfriend told me she liked me, seemingly out of the blue, on AOL Instant Messenger, I’d thought it might be years and years more before entry to this mysterious World of Girls was finally granted to me. True, I’d liked the idea of having a girlfriend far more than I’d liked this girlfriend in particular. But now that I had finally made it into the World of Girls, I wasn’t about to let myself slip back out, no matter how little I enjoyed the infrequent time I actually spent in her company.

So when I opened that envelope and pulled out the first letter, the swell of relief was overwhelming. It was only when I went to put that first letter back in its envelope that I noticed there was a second one in there too.

That first breakup hurt a lot, the way new pains always do. It didn’t matter that I’d never really liked that girlfriend—rejection hurts no matter how much or how little you like the person it’s coming from. When I opened the letter it was movie night at camp and we were watching something I’d always liked, and I remember thinking, well, that’s it, this movie is ruined now. That line was originally going to have a nice little conclusion about how now, of course, I don’t even remember what movie it was. But as I was writing this I realized I actually do still remember what movie it was. It was Pirates of the Caribbean.

After that first girlfriend, nobody else broke up with me for almost a decade and a half. For a while I mastered the art of the mutual breakup, where neither party can explain who started it, or why a supposedly joint decision has left everyone involved feeling so shitty. My high school girlfriend and I broke up after graduation because neither of us were the type who could imagine having been with the same person since high school; replace “high school” with “college” in that sentence and you have the story of the girlfriend who came after her. Then in my early- to mid-twenties I was always the one who left, though those relationships were all so inchoate that it’s not even really accurate to describe what I did as “leaving.” I just forgot about them, or never texted back, or let things slowly slip away. I became an expert at encouraging the women I dated to have low expectations of me so that when I met them, they couldn’t be mad.

I eventually got broken up with in a bad way, years later, by someone I thought I was going to be with for a long time. I know she wouldn’t want me to write about her, so I don’t, even though we haven’t spoken in years, and even though I doubt she has any idea this newsletter even exists. I wasn’t very good at meeting her needs when we were actually together, but I can at least meet this one now that we’re not.

These days, I date all the time, which means I get broken up with all the time too, but the frequency with which those breakups happen doesn’t render them any less shocking when they do. A breakup after a long relationship is paradoxically somehow more understandable: when you’ve been with someone for a long time, they’ve seen the deepest parts of you, and of course they’re not going to like all of them. But when you’re in the early stages of getting to know someone, they’ve still only seen you put your best foot forward. I’m not so egotistical as to think I’m somehow too great for anyone to ever want to break up with me. But I might be just egotistical enough to think that about the person I make myself out to be during those first few dates.

History has shown me that I almost always get over these small breakups within a few days, but that doesn’t change how they feel in the beginning. My journals are stuffed with notes about pain caused by losing the affections of women I now barely remember. This newsletter probably wouldn’t be as good if I didn’t have quite so many romantic travails. But it’s only very occasionally that I think that tradeoff is worth it.

Yours in suspecting that there’ll be at least one person reading this who has known me for a long time and will completely dispute my characterization of every single event described in this piece,