How I Botched A Budding E-Romance

I save a lot of things in my email drafts – half-baked ideas, phone numbers, the occasional angry rant. But among all of the quick notes I’ve accumulated over the years, there’s a full-blown story, one that I didn’t write alone—a 60-email thread with a stranger I met on Craigslist.

I’ve always been okay with meeting people on the internet. On the heels of a breakup in 2007, I had my first OkCupid date at age 20. After that, I dated another guy who I’d found on Facebook. To me, using the internet to meet guys wasn’t terrifying or even embarrassing—it was second nature, a way to broaden my dating pool while I was stuck at a tiny, private college. Growing up, I had internet friends from across America who were as real as the kids I played pogs with, so dating was simply an evolution of what I’d been doing all along.

In 2009, I was finally settling into my post-grad life. I had a job (a terrible one), and my memories of roaming the streets in search of an apartment were beginning to fade. Life wasn’t good, but it was the most stable it’d been in a while. And it was also lonely. I’d been on a few dates, but they were nothing to call mom about. Couple my loneliness with boredom, and you have the reason why I found myself aimlessly scrolling through the Strictly Platonic section of Craigslist.

Most of the ads were typical: “Wanna go skiing? I’ll provide, you host,” or “I just moved here, I’m really shy.” But it didn’t take long to find one that interested me, that actually excited me. He was looking for someone to exchange emails with, I think—I don’t remember his exact words but the intention behind the ad seemed innocent and not of the “blowing cocaine off of each other’s bodies” nature. I emailed the poster, using the conversational prompts he’d provided in his ad and heard back the following day.


I actually got so many responses to my post that I wasn’t able to keep my promise of replying to everyone (yet).  You’re very clever in taking the “reply to the post several days after it was written” approach, because now your e-mail really stands out… and hence this response.  Your response was actually one of the better ones, thank you for that.

I don’t even remember what my post was, to be honest, so the context of my reply might be way off.  We’re going to meet for sex with no strings, right?

“Roger” proceeded to respond to my email, bullet by bullet. I found myself smiling like an idiot at his responses, but by the time I’d come to the end it became clear that he had no intention of meeting offline. Still, I was endeared pretty much instantly and we began an email correspondence that would continue for the next couple of months.

At the end of Roger’s third response, things got meta.

This is crazy, but I got an email from you once (thought your weird name looked familiar). It was in reply to a post about someone who sketched me in Central Park.

It was then that I “knew” who Roger was. That past summer, I’d responded to a Missed Connection he’d placed. A pencil sketch of a guy sleeping in the grass was attached to the post. The story goes that he’d fallen asleep in the park and some girl stopped to sketch him, leaving the drawing pinned beneath a book or something like that. I figured that if he’d been cute enough for a stranger to stop and draw him, he was probably pretty goddamn adorable and I should probably try and get in on that. (Yes, this is the way my brain works. Judge me.) My come-on hadn’t worked that time around, but here we were, a year later, emailing. It was like some sort of strange internet kismet had bloomed.

The coincidence was brushed aside and we continued to email at least once a day. We poured over everything we could think of – work, religion, race, identity, political ideologies. When I received an email from him, I would stop whatever I was doing and read it in full. Sometimes, they were so long that my phone would truncate the message and I wouldn’t be able to read the entire thing until I got home. I’d pretty much mentally check out of whatever I was doing until I could access a computer, wondering how many of his words awaited me in my inbox.

I had no idea what Roger looked like (other than a pencil drawing), but I found myself becoming more and more attracted to him. I started to become jealous when he’d talk about other girls—his ex, who was allegedly on America’s Next Top Model, the girl with a boyfriend who was coming to town and needed a place to crash. I’d dish out ‘tough love’ advice in hopes that it’d deter him from feeling something for these girls, but who was I to do that? I was some cyber pen pal and they were ex-lovers who’d more than likely had their mouths around his penis at some point. I was not winning this battle.

The only thing left to do was level the playing field. I wanted to meet Roger, and I said as much. He only lived a few blocks away from me, and knowing that he lived nearby was an unusual kind of torture. He was reluctant at first, but agreed to meet me for a game of pool. At some point, he even seemed enthusiastic about it. We chose a day and exchanged numbers.

When the day arrived, I freaked out. It wasn’t my first internet-to-real-life rodeo, but my expectations were so high that they practically paralyzed me. I texted him and made up an excuse as to why I couldn’t meet him, rain check? He obliged, but my sudden flakiness served as a red flag. He knew something was up.

We tried to continue our correspondence, but it felt a bit more forced; tainted by the way I’d pulled out at the last minute. Roger insisted on beating my ass in pool, I started taking longer and longer to respond to his emails until finally, I stopped altogether. The email in my drafts folder is the beginning of a response to him, which abruptly ends not mid-sentence, but mid-word.

Yeah, eh. I haven’t had my computer/internet for about a month now, I’m starting not to mind. It’s like losing your cellp

I wish I had a better excuse, but all I can come back to is that I was immature and scared of disappointment. I genuinely thought it better to completely disappear rather than nut up and meet the guy I’d been fawning over for two months. I realize that what I did was completely selfish. I’d coaxed this person into believing I was worth befriending, only to prove that you really can’t trust people, that they can turn on you without warning, that they can dissolve into thin air without announcement.

I should’ve followed through with my plans to meet him or at the very least, explained myself to the one person I’d built a relationship with on words alone. But explaining your feelings, your expectations for someone you haven’t actually met, it’s difficult to articulate. So I took the easy way out, instead, at the expense of someone else.

I found Roger’s number buried in one of our emails but feel conflicted as to whether or not I should use it. I’d say I was sorry, maybe buy him a beer or something. The thing about apologies is that no matter how badly we want to give them, sometimes we know we don’t deserve to be forgiven. Thought Catalog Logo Mark

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