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The Messages We Wish We Could Un-Send

"I once sent my girlfriend-at-the-time a text that said 'I'm going to make your vagina cry.' By mistake, I sent it to my mom."
June 26, 2015, 4:40pm

Photo by Flickr user jhaymesisviphotography

We've all sent messages that we desperately wish we could un-send: the unintentional reply-all, the autocorrect fail, the shit-talking text message you accidentally sent to the very person you were shit-talking. It's a byproduct of living in the digital age—communication gets warped, rerouted, delivered to the wrong person, in the wrong context. Sometimes, you realize your mistake a split-second after you hit "send," but more often, it's not until you get a response that you realize what you've done. Either way, it's too late. The damage has been done.

Not too long ago, Google announced a tool that could change all that: Gmail's magical " undo send" feature. It's not exactly new—it's been in beta-testing mode for six years, and there are scores of other apps that purport to do the same thing for emails and text messages. Now that it's officially launched, though, we wondered: How many relationships and reputations could've been saved with this one tool?


We asked people who've made horrible and hilarious messaging errors to tell us about that one message they wish they could've un-sent. These are their stories.

Things You Accidentally Sent to Your Mom

When I was in high school, my parents were out of town and I threw a big party. I thought I'd cleaned everything but my sister went on our back porch and found a bag of weed my friend had left. I went to text my friend saying, "Dude, you left your bag of weed on my deck. My sister found it," but instead of sending it to "Molly," I accidentally sent it to mom. My mom immediately called me and I realized I sent the text to her. I answered and she asked who I meant to send that text to. I tried to play dumb for a little while and then ended up telling her I just had a few girlfriends over and we smoked. IDK if she bought it, but she didn't ground me. — Morgan

I once sent my girlfriend-at-the-time a text that said "I'm going to make your vagina cry." By mistake, I sent it to my mom. — Jemayel

Things You Didn't Mean to Reply-All

When I was in college, one of my professors sent out an email to our 200-person anthropology lecture, announcing that our midterm scores were available to view online. Someone in the class regrettably hit "reply all" when he wrote back to complain about getting a failing grade. I basically died of embarrassment on his behalf. — Anna

I sent my boss an email, jokingly pointing out an error a coworker made. I accidentally copied that coworker on an email. He took it so personally that he made it his mission to try to have me fired for harassment and bullying in the workplace, even after my explaining there was no malice or ill intent. It was a joke, you weirdo. — Janea


I took a highly pornographic photo of my butt once, and accidentally sent it to my mom instead of my boyfriend. I covered it up by saying, "Have I always had that freckle? I'm concerned that it's growing." — Erin

Junior year of college, I was still heartbroken by my love from my freshman year. The whole situation had been pretty traumatic—she was so happy with this guy who wasn't me! So I wrote her a long email one night about how I was irrevocably in love with her and she needed to come to terms with her not-straight side and break up with her stupid boyfriend. I saved it as a draft… until another night, when I very drunkenly sent it to her. I had a response, deservedly, not a very nice one, waiting for me when I woke up the next morning. We haven't spoken since. — Renata


I sent my brother a text once saying I was "fiercely horny." — Mikol

Things You Sent to the Person You Were Shit-Talking

In high school, I was rooming with two of my best friends on a school trip. One of them had been acting like a mega bitch, so I texted the other one telling her how miserable the trip was gonna be with our bitchy friend. Except I accidentally typed in the bitchy friend's name. We were stuck in a room together for a long weekend and our friendship never recovered. I definitely wish I had rethought that text and could take it back. — Emily

In ninth grade, this girl I had a crush on texted me to tell me she had broken up with her boyfriend. I immediately went to text my sister and wrote: "Lindsay and Scotty broke up!" But when I saw the response—"I know, I just told you"—I realized that I had accidentally sent it to Lindsay. I played it off cool, and she never realized I had a huge crush on her. — Cody *

This girl was rushing my sorority and I accidentally texted her all the horrible things people—including me—said about her behind her back. — Anna

After I was laid off, I wrote this long thank-you-for-the-opportunity email to my boss. She wrote back saying, "Got your uniform and good luck with everything." I was upset, and so I screenshot it haughtily to send to my friend and wrote "lol succinct," but I sent it to my ex-boss instead. I followed up ASAP apologizing for my "rookie mistake," but then I blocked her number so I would never know the response. I was mortified. — Kate

* Name has been changed.

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