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. TC mark


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  • Frida

    I’m guilty of this.
    It feels horrible, but it’s almost a kind of relief to be out of the little world you built.
    I don’t know how it’s possible to go from being so excited to feeling it’s a duty.

  • Frida

    I’m guilty of this.
    It feels horrible, but it’s almost a kind of relief to be out of the little world you built.
    I don’t know how it’s possible to go from being so excited to feeling it’s a duty.

  • lianne

    I’ve done something like this.  He sent me an email a couple months later asking if I was alive and I couldn’t bring myself to face my shame and respond.  Sometimes I still feel bad.

  • Lauren

    Um, I’m gonna go ahead and say I think you are way over-thinking this one.  Maybe he won’t accept your apology and the relationship has soured.  Or maybe you casually apologize for falling of the face of the earth and offer to buy him that beer.  

    Something tells me there’s a part of you that doesn’t want to be forgiven… because if you anticipate that you won’t be forgiven, you won’t have to put yourself out there and risk rejection/vulnerability/disappointment.  
    I say GO FOR IT.  Reach out!  You only live once.  And getting a clear “no” is often better than the “?…” Temporarily disappointing, but worth the risk.

  • Guest268

    Been there as well. However, the only reason I freaked out was because I felt that I’d end up disappointing him… :(

  • Dan Mckean-Tinker

    I’m kinda there right now. But we have met, once. It was fairly early on in talking and since then (only 2 weeks… but so much talking) the mental chemistry has sky rocketed and I have no intention of letting that pass by. There is always the possibility of disappointment in one direction or the other… but if you’re that excited and enraptured just take the gamble, the practical loses are negligible, but what about the positives that could come from that!!

    Also, connections like that don’t die, they hibernate. Give him a call!!

  • Vicky Nguyen

    Man up for women over the internet everywhere. The worse thing you can do is do what you’re doing right now–avoiding it again. If you apologised and he rejected that apology, honestly? That would be the worst case scenario. If not, imagine the relief you’d feel when you finally do it. You might even get to meet him. I mean, that’s why you’re writing about this, right?

    • Dontyoumean

      Woman up*

      • lianne

        oh my god you are the kind of person that says “fisherwoman” too aren’t you.  shut up.

      • Vicky Nguyen

        No. I meant “Man up”.

      • Vicky Nguyen

        No. I meant “Man up”.

  • Jenn

    I am about to meet someone I’ve been talking to for a long time. I am so stoked! You have to email him, Steph!

  • Jenn

    I am about to meet someone I’ve been talking to for a long time. I am so stoked! You have to email him, Steph!

  • NoSexCity

    My only question is: well, will you or won’t you be giving it a shot? (Or, if nothing else, regretting not reaching out again for at least a few more months?)

  • Tom Smith

    Every girl I’ve had an online relationship with has fallen apart quickly if we didn’t meet within a couple weeks of starting correspondence. It gets too intense or too sporadic and there’s no way to meet up without expectations getting the best of you or without losing interest for whatever reason.
    That said, you should still apologise and try to make a go of it, if he’s interested. You’re clearly already kicking yourself over it, and it seems like he’s worth fighting for, not to be too cheesy.

  • Afaulstich54

    im on the verge of someone ive also been talking to via email/text messaging, im honestly in a way hoping to be disappointed.  i want to be sure that he’s human and capable of having flaws or inconsistencies that aren’t obvious in written conversation, i want to see the parts of himself that he doesn’t work to portray, maybe a nervous tick or habit, or even make simple eye contact.  written conversation can be entertaining, and its potential can be thrilling, and reassuring to have a regular penpal who listens and adds; but i don’t feel its a suitable replacement for the simple humanity of real interaction because it tends to be so detached.

    • Afaulstich54

      verge of meeting*  sorry.

  • The Impersonals

    Emmm I dunno. I’d go with your gut on this one. My theory is that anyone you meet on Craigs List will look somewhat like Craig Newmark, the founder.

  • mashka

    It’s confusing being in a situation like that- I mean not even specifically referring to meeting someone from the internet- just the idea of getting back in touch with someone you’ve been out of touch with for so long: is it worth it? or was the lapse in contact a sign that things just weren’t meant to be?

  • Kyle Angeletti


  • Betty White

    ………..……    …...

  • Betty White

    I can’t believe….My best friend’s mom makes $77 an hour on the computer. She has been out of job for 9 months but last month her check was $5487 just working on the computer for a few hours…………..

  • SusanDerkins

    You could just send him this article. “Hey, thought you might want to read something I wrote.” Passive Aggressive, sure, but he knows that about you already ;) 

  • Peroxideblonde29

    I really dug this article, mostly because I’ve felt this way on numerous occasions. It’s nice to know I’m not the only one(I always knew I wasn’t the only one with these issues, but actually reading about them made me feel a bit more cemented about that thought) who had these kinds of problems and worries. The bit about it being hard to articulate how you have expectations for someone you haven’t even met was spot on. I feel that you start chatting with someone and if your’re a person who knows what they want and like, then you’re pretty sure about knowing that you’re going to like a person( that could just be the hopeless romantic in me typing). It’s even hard to articulate right now. You just feel that it’s going to end up with one person not liking the other, and usually not in your favor. I’ve had experiences like this happen before where the person just pulls away and disappears, both on my part and their part, and after that happens it’s usually shot to hell. I’ve had it where someone’s reappeared in my life, acting like nothing happened and everything was ok and wanted to pick up where we left off, but by that time I’m usually so turned off by the situation that I’m just over it completely over it.(to this day I have no clue why people think it’s ok to treat people like shit and to just forgive it). I’ve also done some disappearing myself, but these disappearing acts stem from the fear of myself liking someone and not being liked back, as to where the guys I’ve mentioned just left me hanging ‘cus they got a girlfriend or some new ass to tap. I’ve noticed that when things pan out in this fashion that they are pretty much doomed, as it’s too much bullshit to deal with with out the need to. As complex as people are, we like to keep things as simple as we can. I some times wonder if I would have just boned down and took the chance if  things would have gone much better.

  • Mr. Ian M. Belcurry

    This line “…were ex-lovers who’d more than likely had their mouths around his penis at some point.” Made me laugh. You weren’t too horrible of a person. You flaked once, which sucks but seems reasponable in the siutation. I liked this. There might not have been chemistry physically between you two.

  • Michael Koh

    wow… distressing… so real

  • Ritu

    Call him! We want to believe he is great and forgiving and you’ll both realise you were worth the wait.

  • Joant Ubeda

    Oh, man, something similar happened to me. She visited my city from another continent, met briefly when she came into my work, asked for directions for somewhere, asked me if I had Facebook, we added each other, we “liked” and commented on our Facebook stuff. She visited once again, we talked for hours at the beach. I took care of her when she was sick, months later I flew across the world to visit her. We had sex, and now we’re best friends.

    Love it.

  • ofdivinemadness

    the world is fucked…

  • ofdivinemadness

    the world is fucked…

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