#Love: My Biggest Digital Faux Pas

Our attachment to computers can play tricks on us. With the ability to navigate anywhere, order anything, calculate any math problem, and answer any question right in the palm of our hands, it would be easy to feel god-like. Infallible, even.

But oh, if that were the case! While our computers, and the internet, do make us instantaneously more knowledgable (and even correct our misspellings as we type), the code can only do so much with the mess we throw at it. In fact, our constant access to social media and other people probably opens us up to even greater possibility of screwing things up.

We’ve all been there, whether it’s an accidental CC instead of a BCC or leaving yourself signed in to the wrong account on the wrong computer. So in honor of our grandest mistakes, and as a reminder to use the 15-second-rule and to resist the urge to text while drinking, we’ve compiled some of the best digital disasters we’ve heard.

As you can expect, we’ve changed the names of those involved.


For a while, I was dating two girls that I met on J-Date with the name Emily. I had taken the first Emily to brunch on Saturday morning and the second Emily to drinks on Saturday night. On Sunday, I woke up pretty hungover from the night before but thinking about brunch with Emily #1. So I fired up my iPhone to text her, but saw that I had a message from the other Emily, Emily #2. She had thanked me for last night.

I got up and grabbed a glass of water and then returned to my phone to message both of my Emilys.

I carefully typed out my message for Emily #1: “Had a great time at breakfast. Today’s cereal pales in comparison. When can I see you again?”

As soon as I sent that off, I opened up the other Emily’s text conversation and hurriedly sent: “Ya last night was fun.”

Unfortunately, I had texted the wrong Emilys. Emily #1 sent me a “?” in response, and instead of realizing that I was talking to the wrong Emily, I proceeded to describe in some graphic detail some of the fun I had had with Emily #2, who was also pissed. Neither ever talked to me again.


In eight grade I had a crush on a girl who would barely talk to me in real life, but sometimes I could get a pretty good chat going over AIM. She was one of the popular girls at school. I told her I had a friend named Jason who played soccer at the public high school in the next city and “introduced them” on AIM. He wasn’t a real person, just some dude that I had made up. But after talking a few times, I started flirting with her as this other guy on this fake account.

It was totally weird but it gave me the chance to flirt with her and have her flirt back. The lying started getting difficult, especially when she wanted to hang out with me so she could meet him in real life. Eventually, she asked to come over to my house and didn’t bother me about meeting him or going to see him. I had hope for a few hours. Until I realized she had snook onto my computer while I was in the bathroom and found out that “Jason” was me.

The whole school found out. Eight grade was hard.


I was studying overseas for a while and started a pretty wild affair with a professor there. We would communicate a lot via email, and in one of our conversations he had sent me a “lesson plan” full of incredibly inappropriate and also very sexy things he planned to do with me. I was editing an email to one of my exes, and somehow pasted in this “lesson plan list.”

When I realized what I had done, it was the strongest rush of anxiety, embarrassment and horror. My heart was racing because I could only anticipate how shitty; it would be for him to read something like that. It was truly awful.


This isn’t the story of my biggest digital mistake, but the one that affected me the most.

Many years ago, I was on a business trip and exhausted from jet lag. I woke up in the middle of the night to my phone buzzing, and see that a client has sent me an email. I normally would just go back to sleep, but this was a new and very important client, and if she was sending me an email at 1AM, I felt like it was probably urgent that I respond.

What I saw when I opened it was very much the last thing I wanted to see. She was posed before a mirror in some horrid red lace thing but still naked in all the parts that count. We’re talking full frontal. And not to sound judge-y or awful, but she was many years older than I was and… just, not at all what I wanted to see in the middle of the night.

A few minutes later I got a separate email from her that said “I’m so sorry that wasn’t meant for you. Please please please delete it. PLEASE.”

I wrote back and said it was no sweat, and that this never happened. But yes, I had to see her again and yes, it was super awkward.


The biggest mistake I ever made on the internet was snooping through my ex’s Facebook. She left herself logged on on Facebook on my computer, and even though we were happy together for a really long time… like, seven years, I still couldn’t resist looking. Clicking into the messages was a huge mistake, mostly because there were a bunch of messages to a guy she was cheating on me with.

I obviously needed to find out, but finding out like that was definitely a mistake. It’s not funny or all that exciting, but it was definitely the biggest mistake I ever made on the internet. Totally regret it.


In college I was dating a guy that I was totally obsessed with and after we broke up, I kept his email password saved on my computer. I checked it all the time, for months, very carefully checking the “sent” folder instead of opening up new emails in the inbox. He never suspected me at all, until one day I came back to my computer, opened up my email, and absolutely forgot that I was using his account.

I sent off only two different emails before I realized what I had done: The first was to my sister, who I could immediately alert to not write back and simply delete the sent message. No harm done. Unfortunately, the second email was an invite to a smallish party that was sent out to about a dozen of our closest mutual friends. Confused by the fact that they had received an email from his address that was signed “XX, Olivia” they all pretty much thought I was a psycho for a little while.

This last one is from the book “Unfriending My Ex”, by Kim Stolz:

One night at dinner with Andrea (current girlfriend) and another couple, I felt a sudden urge to check Brenda’s (ex-girlfriend) Facebook. Under the table, I managed to guide my fingers and navigate my phone to my Facebook app. I was so proud of myself for being able to do this blind — what a thing to be proud of!

In my glory, I fumbled the next step. Instead of clicking the search button where I was planning to write Brenda’s full name and click on her profile, I found myself in the “Update Status” box. I typed in “Brenda Carlson.” Before I had a chance to peruse what I thought would be her Facebook page, the conversation turned to something pertaining to my work and I reengaged in the dinner, an- swering a few questions. A few minutes later, my phone buzzed. It was my friend Amy. “Kim—wtf are you doing re Facebook?”

I had no idea what she meant but I was suddenly dizzy with anxiety. I looked down at my phone. My pro- file’s most recent update, which appeared in all 1,022 of my friends’ feeds (including Andrea’s), read “Kimmy Stolz is Brenda Carlson.”

I quickly deleted it. I think I got lucky be- cause Andrea never brought it up. But I assume, given the frequency with which we all check our Facebook accounts, I shared my transparent stalking with at least four hundred to four hundred fifty friends during the ten minutes it was up before I managed to delete it.

#Love is a new column on TechCrunch dealing with digital matters of the heart. It explores our relationships, their relationship with technology, and all the gory details that come with it. Jordan Crook will be leading the charge, and is looking for guest writers to tell their own stories each week. Maybe you found your soul mate on Tinder, or got dumped on Facebook, or have an outrageously interesting sext life. We all have our stories. If you’re interested in contributing, send an email to jordan@beta.techcrunch.com with the subject line #Love for more details.