it's complicated

That Time I Accidentally Emailed an Old Love-Letter Draft to My Ex

Photo: J.V. Aranda

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“hi i have been thinking about you lately” — that’s how the draft began. No caps, no punctuation, not even a subject line, just a telepathic beam of desperation from my brain.

The you in question was my first serious boyfriend, Sam, whose email address was waiting in the “To:” field. And the draft itself was representative of a genre I’ve come to think of as the Sad Draft — an outpouring of emotion to an ex or a crush or an old friend that one never intends to actually send. Stream of consciousness is its defining style and abrupt escalations in tone are virtually required.

I think a lot of people write drafts like these, but maybe fewer revisit them regularly. I love to reread mine. I earn a small satisfaction by privately admiring my not-that-bad raw writing from moments of crisis, and the drafts are an efficient reminder that time changes everything. Ideally, a Sad Draft will document feelings you’d completely forgotten you were even capable of having.

I opened this particular draft last year as part of a game I was playing with a new boyfriend. We were searching various exes’ names in our Gmail inboxes and reading aloud the corniest love notes or most depressing emails we’d exchanged with them, which was really just another way to revel in our own happiness. I’d written the message to Sam in 2011, after he’d broken up with me with the promise that we could still be friends. At the time, that was a vital agreement for me: We’d dated on and off throughout high school and college, and I was devastated when our relationship ended. Continued “friendship” with him seemed like a way around my conviction that I’d never be in love with anyone else.

Unfortunately, Sam never delivered on his promise. Every few weeks, I sent him funny texts or music I thought he’d like; he responded maybe one percent of the time, and was never the one to initiate contact. So I’d written this email in a small fit of rage, probably after staring hopefully at the green circle next to his name on Gchat until it disappeared without a peep. “i’m not mad or upset about you generally ignoring me and obviously you have no obligation to me,” the draft went on, “but it’s frustrating after all that talk about wanting to be friends. there’s a lot of stuff that only you get and it would be nice if you cared. i just know that you are never going to initiate. i will be surprised if i ever get a text message or email from you without me doing something first. wow, that makes me feel like shit.” (Okay, fine, so maybe my raw writing can be pretty bad sometimes, too.)

That I read this draft aloud to a new boyfriend is a testament to how confident I was that I’d since become a different, more grown-up person. He and I laughed together at my pathetic attempt to reprimand Sam, who clearly had had the upper hand, but when the Sad Draft switched gears to full-on earnest lamentation, we both quieted down. It just got too sad: “i still want all those things we used to talk about. a big white bed in a clean white loft. a fat dog. falling asleep and waking up next to you.” (That’s aspirational adulthood for a 20-year-old, I guess.) The most cringeworthy sentence in the draft, however, was its last line: “and i guess what i’m really saying is, i don’t think I’m ever going to be over you. i have a sick feeling it’s not the same for you. no other thought has ever made me feel more lonely.” We groaned at my melodrama, I felt intensely glad to no longer be 20 years old, and then I closed the draft, moving on to an animated reading of a limp apology email from a different, less significant ex (“I’m kind of an idiot, sometimes.”).

Two days later, as I woke up my phone on the way out of a yoga studio, I saw that I had an email from Sam. What a coincidence, I thought. I was just talking about him!

The email had no subject. That’s always intriguing. “I’m really confused by this email,” his message began.


“I think I need some context before I know what to say. Do you want to get coffee or something sometime?”

Wtf is he talking about?

I scrolled down to see what he was replying to — oh. Fuck. I had somehow sent him the Sad Draft. “i don’t think i’m ever going to be over you,” the white bed, the fat dog, the works.

Sam and I were no longer really in touch. In the years since I’d written that draft, I had stopped reaching out to him, initially through the force of self-control and later because I’d genuinely moved on. The last time we’d spoken was at least a year prior, when I’d texted him my condolences after the death of his mom’s pit bull, whom I’d known and loved.

I responded to his email immediately, sweating in anxiety on a street corner. “Oh my god!!!! This is my worst nightmare. I was looking for my saddest old emails and found this draft from like 2011 and must have accidentally sent it. I’m so sorry!!” When he didn’t reply right away, I sent a follow-up email clarifying in what I hoped was a blasé tone, “I no longer feel ignored by you (or care about you ignoring me, which I mean in the kindest way possible).”

I was concerned about communicating that the email had been written six years prior, but more importantly, I also needed to make sure he didn’t think I’d sent it on purpose. In high school and college, I’d been a sloppy practitioner of the on-purpose accident: During one of my “off” periods with Sam, soon after we’d lost our virginities to each other at 16, I pretended to have mysteriously contracted syphilis as an excuse to talk to him (“My doctor says I should tell you…”). I’d also pulled the “oops wrong IM box” trick far too many times to be plausible. In short, he’d known me to take desperate measures to get his attention, and he had no reason to believe I’d changed.

Eventually, he did reply. “Totally ok. I’m really smiling.” He seemed to believe me and to think it was funny. A little high on his positive and relatively timely response, I suggested that we meet up for coffee anyway.

Sam agreed, and we planned to get together within a week. On the agreed-upon day, I carefully choose an outfit that I hoped would look like something I might wear normally, but that also happened to make me look really hot and cool and different from how I’d dressed while we dated.
I got to the coffee shop early so that I could be busy working on my laptop when he arrived. Sam and I were finally meeting up like regular old friends, and I imagined that looking up from my screen to greet him, casual and aloof, would help me prove that, six-plus years later, I really was over him.

At the appointed time, I texted him to tell him I was at the café — he lived nearby — and watched his little “…” bubble oscillate until a message appeared. It was one I’d been half-expecting: “I’m just feeling so lazy and cozy in bed right now,” he wrote. “Would you ever forgive me?”

As an old pattern reasserted itself, I tried to channel some of my ancient frustration from that original email into the sternest response I could muster: “lol i knew it. It’s fine but i will probably never try to hang out with you again.” Making my way back to the subway, in heeled boots I would typically never wear, I tried to find some satisfaction in the fact that this Sad Draft, though years old, was apparently timeless.

I Accidentally Emailed an Old Love-Letter Draft to My Ex