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8 People Reveal Their Most Embarrassing Email Mistake Ever

Updated: Jan. 25, 2024

An estimated 205 billion emails are sent every single day. With so many opportunities to put the wrong email address in the "to" or '"forward" to the person you were gossiping about, it's no wonder so many people have hiccups when they move too swiftly in their Gmail or work accounts. Here, real people share their greatest blunder ever.

1 / 8

That time sarcasm got the best of her

Ashley Davidson’s first job out of college was as an intern coordinating group lunches, happy hours, and other social activities. When one of the interns she was closer to in her 30-person class sent her a funny news article, she couldn’t wait to take part in the humor. “I meant to reply to just him with a snide, rather politically incorrect remark—except I hit reply all. Because our intern coordinator, who worked in human resources, was often included on the social emails, he swiftly responded to me making sure I knew how unprofessional my reply-all response was,” she shares. “I was really sitting at my desk absolutely mortified and couldn’t look anyone in the eye the rest of the week. It’s been nine years and I still remember it,” she says.

2 / 8

That time dirty talk was sent to the wrong inbox

When Katie Kirby was working on a project for Jim Beam, she was responsible for contracting mixologists all over the country to develop recipes for a tequila brand. Though she was based in New York, she was sending quite a few professional emails to a well-known bartender in Los Angeles. “One morning he sent me an email that was clearly intended for a woman with whom he had spent the previous evening. It’s too graphic to share, but let’s just say it included the word ‘thirsty’ and conjured up a very clear visual,” she explains. “I contemplated ignoring it but just couldn’t resist—so I replied and said ‘I’m pretty sure this wasn’t intended for me; but whoever she is, she sounds like a very lucky girl.'” His response? An appropriate, “Oh. My. God.” Here’s how to actually apologize in a way that matters.

3 / 8

Saved by the date

The managing director for the travel agency, MickeyTravels, LLC, Greg Antonelle gets invited to many events, but as an entrepreneur, he has to determine which ones are the smartest use of his company’s finances and budget. So when a company who was offering to work with Antonelle emailed to suggest he pay a rather hefty expense to attend a conference, he rolled his eyes silently. The only issue? He did more than that. “I guess I assumed I was blind copied on the email, so I went to forward it to my wife, but instead ‘replied all.’ My sarcastic response was something to the effect of, ‘I don’t think I would pay a dollar to attend this seminar, since I could probably run it myself. I’ll have to come up with an excuse not to be there!’ As soon as I hit send, I realized my mistake,” he shares. How did he recover? Luck was on his side: It happened to be April Fools’ Day! “I quickly ‘replied all’ again, and said ‘April Fools’! Of course, I’ll be there. I’m signing up now…wouldn’t miss this for anything!'” he says. “While it was a quick recovery and a bit disingenuous to be honest on my part, it ended up working out very well, as I attended the conference and have built a very strong relationship with the other company involved. I still work with them to this day and we have fun laughing about it.” Try out these April Fools’ Day pranks in your office the next time April 1 rolls around.

4 / 8

That time a he was a she

For Antonia Donato, part of her gig is emailing pitches to various people. While with most names it’s fairly easy to identify if a person is male or female, sometimes it’s an unfortunate guessing game. “I remember introducing my boss to a new writer and addressed her as ‘he’ when she was a she; the person wasn’t too offended, but it was embarrassing nonetheless that I hadn’t done my research on the writer prior to making an introduction to my boss,” she shares. She apologized—and made sure to always do due diligence before any professional interactions from that point forward. (No pun intended). Make sure you’re not guilty of these nine annoying email habits.

5 / 8

When a snide remark kept going

When Martin Stein was working in journalism as the Arts and Entertainment editor for the San Francisco Examiner many years ago, the newspaper was going through a relaunch and redesign. A few months into this process, a new editor-in-chief was hired and came in hoping to bring in his own team. Luckily, Stein was kept onboard and actually received a promotion and raise during this turbulent time. “I sent out an email to all of the public relations people I had been dealing with, and it wasn’t long before I received a reply back. Sort of. It was actually my email being forwarded to several other PR people—with myself still included—saying, ‘Well, he didn’t last very long, did he?’ That was quickly followed by a few replies from the other publicists wondering what was happening at the paper,” he shares. “I sent back a reply to them all explaining that I was simply being moved and things were fine. After a long pause, I got a heartfelt apology for the unprofessionalism, but I was never upset. I understood where they were coming from.”

6 / 8

When nutrition talk got dirty

Megan Hunter, a writer who covers a wide variety of topics for various publications, often juggles her interviews, all while managing a full-time job too. The only issue is when her wires get crossed, especially when she’s on deadline. “While multitasking too hard one Monday and toggling between assignments, I sent an email of very explicit questions regarding the mechanics of proper lubrication as it pertains to anal sex to a nutritionist I was working with on a story about healthy ways to prepare chicken,” she shares. “Not the type of basting she thought she’d be asked about, I bet!” Though she quickly apologized, Hunter was reminded to always double-check the subject line and “to” field before hitting “send.”

7 / 8

That time when she was unintentionally rude

For Emily Baker, a private school teacher in New York City, balancing her role within the classroom while also taking on other projects and tasks is a difficult feat. During a busy time in the school year, Baker was attempting to delegate when she perhaps should have graded her own email before sending it out.” I sent a blunt email to my co-worker regarding all of the tasks that we needed to complete for a project we were spearheading. While the email wasn’t exactly rude, it was a frank checklist explaining what our team was responsible for. I didn’t think anything of it when I sent it… until I realized I didn’t just send it to my co-worker, but to the entire committee,” she explains. “I ended up looking like a bossy bitch when I was attempting to keep everything organized.” Though the team knew her well and likely didn’t think anything of it, her lesson (plan) for the day was learned. Before unsubscribing from an email list, read this first. 

8 / 8

Crazy, insane, and cc’d

Jordan Jacobs’ job as project manager of a busy flooring company in North Carolina requires her to wear many hats, from building schedules for salespeople to keeping the financial books up-to-date and managing her employer’s calendar. One day, when she sent an estimate to a potential customer for a room they were finishing, she cc’d her employer and the salesperson who earned the business. Though it was a reasonable rate, the client wasn’t exactly happy. “This person basically responded with an angry email that was definitely meant to be sent to his business partner, not us. He called us ‘crooks’ and ‘insane,'” she shares. Though this client didn’t respond to apologize, a few months later, he came back and accepted the cost, since he couldn’t find a better price in town. Here are nine other work blunders you need to work hard to avoid making on the job.