Before ‘Undo Send’: 11 New Yorkers on Their Biggest Email Gaffes

Dejected Man Sitting at Desk
Dejected Man Sitting at Desk . Photo: Nick Dolding/Corbis

Gmail’s new “undo send” option, which it officially rolled out this week, lets you retract an email up to 30 seconds after sending it. To celebrate this potentially new sanity-saving function, we asked a bunch of random New Yorkers (including one gossip legend) about past emails they wish they could take back. Here are their stories:

1. In the mid-’90s, I was in my early 20s and dating this guy for a few months when I found out through a mutual friend that he had a girlfriend. So I promptly broke up with him via email, saying “I hope that your girlfriend enjoys your small dick.” I meant to blind-copy the mutual friend but I was in such a rage that I plain-old copied him. The ex was like, “Why’d you have to copy F.?!?”  — Angela, 41, Harlem, educator

2. I told my best friend in an email that she was ADHD and had some other psychiatric problems and that because she was completely incapable of being on time or keeping her life organized, I could not be friends. We didn’t talk for three or four years — and she still refers to it as “the email.” — Elizabeth, 34, musician, Williamsburg

3. The publicist for Wolf Hall sent out a press invite months and months in advance. I thought I was forwarding the email to a friend and wrote, “This publicist is out of his mind” in the subject line. Alas, I mistakenly sent it to the publicist. I then had to backtrack with choruses of “Kidding. It’s actually a genius PR move.” — Michael Musto, scene and gossip writer 

4. I was casually sleeping with this guy who just never gave a shit. He’d get in touch when he was in town and ignore my texts pretty much always. I wanted more. More consistent sex and also more in general because I was unfortunately in love with him. So I had this brilliant idea to write a manifesto about how we ought to be having more sex. Like four paragraphs of very passionate, rousing language about how I just wanted sex, lots and lots of sex, and did he want to get on board with that or what? And then he was like, “100 percent yes. I’m in.” But I got moody because it wasn’t what I wanted at all. I was basically offering myself on a platter but I wanted him to be my boyfriend. Anyway, we slept together maybe one or two more times after that and now we don’t speak. I erased the email from my own sent folder so I’d never be reminded of how crazy I was, but I have nightmares of it somehow getting out and I wish there were a way to somehow burn things through the Internet. My only solace is that I later found out that I was just one of many side pieces he had while cheating on a long-distance girlfriend, so I think he might be as invested in erasing the paper trail as I am. — Lisa, 37, photographer, Williamsburg

5. There was a huffy colleague I used to work with who gruffly stormed my cubicle and barked at me to give him a file I had on my desk, snatched it, and walked away. I meant to email my next-door cubicle-mate: “What a fucking ASSHOLE.” But of course I sent it to the huffy colleague, who responded: “???” I tried to backtrack and say I meant it for another person, but I don’t think he believed me. — Derek, 39, copywriter, Chelsea

6. I meant to let my old friend N. know that I was intending to go to Brooklyn to break up with the guy I’d been dating, whose name was also N. Sadly, that’s the N. that I emailed. He just wrote back, “Okay.” — Ross, 48, musician, East Village 

7. Once my boss sent me an email asking me to perform a task immediately, using ALL CAPS for emphasis. So I copied a Wikipedia article on business email etiquette and pasted it into an email to my boss, highlighting the part where it says that “using all caps is highly unprofessional as it implies shouting.” That turned out to be a career-limiting move … but it felt gratifying when I sent it. — Aly, 31, business analyst, East Village

8. A new Tinder friend with a predilection for pretty feet requested a photo sent to his email. I complied quickly — and accidentally sent it to a group email of highly platonic friends. My foot photo failed to impress. — Scott, 56, activist, Chelsea

9. I applied to be a part of Smorgasburg and got rejected three times. I forwarded their third rejection message to a friend who was a vendor and had encouraged me to apply, dissing the Smorgasburg guys and going so far as to call them pigs. But instead of “forward” I hit “reply” by mistake … and so my insulting email went straight back to Smorgasburg. I thought my food career was over and I would have to move to another city. But the best part of the story is that they replied by inviting me to come and “audition” by bringing some of my food to their offices. And that is how I became a Smorgasburg vendor. — Anita, 34, food entrepreneur, East Williamsburg

10. Once I accidentally copied a colleague on an email in which I called her ineffectual. She replied to me that she was certainly not ineffectual! I apologized, but backhandedly, pointing out all her recent errors and dropped balls. — Forrest, 42, publisher, Prospect Heights 

11. The last email I sent at my last job was to the colleague who didn’t bat an eye when I’d talk about fears I might be fired, when he knew all along I was going to be fired. I just wrote him “you’re a cold motherfucker” in the subject line. That was it. I don’t regret it — yet. — Scott, 47, book publishing, Park Slope

11 New Yorkers on Their Biggest Email Gaffes