The Dumbest E-Mails Ever Sent

  • Worst E-Mail Blunders

    Drunk dialing is no longer the quickest way to sabotage your relationships and your career. All you have to do these days is click send at the wrong time and you can ruin your life. The only bright side of e-mail mistakes is that we get to make hilarious lists like this one. Perhaps they’ll scare you into being more careful when you send your own e-mails. Or, if nothing else, they might make you feel a little better about your own e-mail blunders. We tried to stick to e-mails that were sent in a professional setting. So here they are, the worst e-mail offenders. Photo Credit: dampeebe
    Don't Tell Them What You Really Think
  • Don't Tell Them What You Really Think

    Mike Dodson was working at a company in Silicon Valley when layoffs were about to be announced. “One of our VPs was having discussions (by e-mail) with the executive staff about this topic and sent them a spreadsheet with a list of all the names he was considering for the layoff. Beside each name on the list he had a brief comment reflecting his opinion about that person and whether they should be laid off. When he sent the message (with spreadsheet attached) to the entire executive staff, he inadvertently used the wrong distribution list and sent it to the entire company!” The VP quickly realized his error and approached Dodson, who worked in IT, asking if they could delete the message from the system. They were able to, but not soon enough. “Several people had already downloaded it. Everyone in the company knew about his mistake, and of course nearly everyone managed to get a copy of the spreadsheet.” Wait. It gets even worse. “The most often discussed part of the blunder was the inclusion of a specific name on the list of layoff candidates; a person that had sadly passed away just a few days prior, and the comment beside their name – ‘dead.’” Brilliant. Photo Credit: soylentgreen23
    Too Much Information
  • Too Much Information

    Margo Schlossberg is on an e-mail list full of small business owners. One day, she and everyone else on the listserv received a strange and unprompted e-mail from the owner of a dance studio, who decided to explain that he was not having an affair with one of his students.  It was so preposterous that Margo saved it, and forwarded an excerpt of it to us. We have removed any identifying information. “Happy New Year to you and I am excited for another year of exciting classes with [my dance company]. There have been some rumors going around about my relationship with Karen and I want to say that we are doing just fine and are happy.  I know that I dance with many of the students but there is no significance to that dancing and I would appreciate if you would refrain from starting such rumors.  My relationship with Karen is very special and I want to repeat that there is nothing happening with any of the students.” The sender then went on to list some exciting new classes being offered in the New Year. Publicizing your personal business is never a great way to promote your professional one. Photo Credit: Pink Sherbet Photography
    Mistaken Identity
  • Mistaken Identity

    James Wolf currently works as a teacher at Illinois State University, but one of the more valuable life lessons he learned came from a previous career. “While I was working at one of the nation's two biggest wireless carriers, two members of our group were dating. One inadvertently replied to all and let us all know exactly how much they enjoyed the last time they had sex,” he told us. “The woman was so embarrassed that she ended the relationship shortly afterward.” Photo Credit: Pink Sherbet Photography
    Odd Man Out
  • Odd Man Out

    Charlene Davis has been a part of her fair share of e-mail mishaps.  One involved a three-way e-mail conversation she’d been having with two of her coworkers.”Two of us didn’t much care for the third person for a variety of reasons, but didn’t want to let on because it would cause friction,” she said.  However, she accidentally let the cat out of the bag. “When responding to my friend/co-worker I said something to the effect that the other co-worker was a ‘few fries short of a Happy Meal,’ and hit ‘Send’ instead of ‘Forward.’ Unfortunately, it was sent directly back to the wrong co-worker! Needless to say, the nasty co-worker was very offended and let us know in no uncertain terms. However, afterwards she never spoke to us again, so it wasn’t so bad once I got over the ‘I feel like crap’ part.” Photo Credit: gary j wood
    "Your Mom" Jokes Go Horribly Wrong
  • "Your Mom" Jokes Go Horribly Wrong

    One member of MainStreet’s editorial team who wishes to remain anonymous had a great story. “This was about 10 years ago. I was working at a big law firm in Manhattan. My best friend was across the country in San Francisco and we had a daily ritual which ensured we’d keep in touch on a regular basis. Every day we’d send each other an email insulting the other’s mother. And these weren’t your run-of-the-mill, ‘glass eye with a fish in it’ mother jokes. These were over the top, graphic and frankly, pretty disturbing. But to us they were hilarious. “Like an idiot I was sending him these e-mails from my work account. One day, after crafting a particularly devastating tome, I accidently sent the email not to my buddy, but to the secretary of a very powerful partner at the firm. I realized it the second I hit send. And as horrifying as it was, I couldn’t help but laugh hysterically when thinking about the poor woman’s reaction to my nauseating screed. Thankfully it never came to that. It was after six and the woman had already gone home and I was able to get a friend in tech support to go into her account and delete the e-mail so no one was the wiser. I really dodged the bullet.” Photo Credit: doc6366
    Using A Dumb E-Mail Mistake to Boost Your Argument
  • Using A Dumb E-Mail Mistake to Boost Your Argument

    George Giles was having problems with his gas meter, which caused his bill to escalate higher and higher each month. Frustrated and unsure what to do, he went online and found the e-mail addresses for everyone in the local mayor’s office (including the mayor) and asked them to send someone to help fix his problem. Now, I’d like to take a moment here to say that e-mailing the mayor with your small domestic problems is probably a snafu in and of itself, but the response that Giles got back was much worse. “Within a few hours I got an e-mail from someone in the mayor's office who had accidentally cc'ed me on the message. She was writing to internal staff saying what a pain in the butt I was and that I should just pay the bill instead of wasting her time,” he said. Giles then decided to turn this to his advantage. “I kindly wrote her back, and cc'ed everyone else in the office, with a professional e-mail letting her know that my issue was real... My e-mail showed her that I also got her e-mail and that she had unintentionally mailed it to me as well as the whole mayor's office. Within an hour I got a call from the mayor himself apologizing for the situation, promising to resolve the issue by sending someone to test the equipment and reprimanding the employee.” Photo Credit: Anders V
    In Need of A Proofreader
  • In Need of A Proofreader

    Debbie Ouellet wrote to us from that great country up north (Canada, for those who you are geographically dyslexic), with a funny story of a small e-mail mistake. She was working at a big outsourcing firm at the time, when one of her coworkers was asked to e-mail an apology to an angry client. Of course, this wasn’t just any client. “This was our biggest client and there'd been a mix-up on their last month's invoice,” Ouellet said. “The accounting clerk spoke English as a second language. She couldn't recall the word 'inconvenience' and relied on Word's Spell Check correction. The message came out as, ‘I apologize for any incontinence this may have caused you.’ Luckily, our client had a sense of humour.” Photo Credit: quinn.anya
    Misdirected Love
  • Misdirected Love

    Stephen J. Dubner described some of the worst e-mail mistakes he’d been privy too in a piece for The New York Times. But in my humble opinion, the readers who commented on the article completely trumped his story. My personal favorite came from a user who identified himself as Aaron. He wrote: “I’m gay and my partner’s name is Mike. At my company, one of my vice presidents who is two levels of management above me is also named Mike. When I first started at my company I was constantly sending personal e-mails to my vice president that were inappropriate and embarrassing given the situation. E-mail address auto-fill is NOT your friend! “I never sent anything salacious but more like, ‘Hey Pumpkin! What’s for dinner? Do you want to go to the movies on Friday?’ Luckily, the VP Mike had a really good sense of humor and teased me about it a bit. But when I first realized that it happened, I was mortified.” Photo Credit: Nono Fara
    Everyone Gets Into College
  • Everyone Gets Into College

    Few e-mails are as infamous as one sent from UC San Diego telling thousands of students they’d been accepted into their college, when they really had been rejected. According to the Los Angeles Times, “The e-mail, which began, ‘We're thrilled that you've been admitted to UC San Diego, and we're showcasing our beautiful campus on Admit Day,’ was sent to the entire freshman applicant pool of more than 46,000 students, instead of just the 18,000 who had been admitted.” The college admissions director later took full responsibility for the mistake, explaining that they had “accessed the wrong database.” Destroying tens of thousands of dreams with one click? That’s just stupendously horrible. Photo Credit: uniinnsbruck
    The E-Mail That Murdered the Environment
  • The E-Mail That Murdered the Environment

    In their roundup of the worst e-mail mistakes from the past year, EmailServiceGuide.com chose an obvious winner, the thousands of messages that were sent between climate scientists at the University of East Anglia. No, the scientists did not accidentally CC the press on their e-mails; rather, the messages were hacked into. So at least the scientists weren't that stupid. But the messages themselves are very bad. According to the Washington Post, these e-mails highlighted deliberate attempts to cover up studies that went against the theory of climate change. "I can't see either of these papers being in the next IPCC report," one scientist wrote in an e-mail. "Kevin and I will keep them out somehow -- even if we have to redefine what the peer-review literature is!" Not surprisingly, these e-mails were later used as fodder for global warming skeptics. Photo Credit: danielalonso
    Sexual... Very, Very Sexual
  • Sexual... Very, Very Sexual

    Two employees at Cornell University made news late last year when they accidentally sent a long string of private and very graphic messages to the general e-mail list at their school. The employees were married to each other but, as ABC News put it, were also “very adulterous.”  According to ABC, “[Their] co-workers opened their inboxes and were greeted with an eye-opening blast of salacious text, very little of which can be printed here except perhaps this: ‘I had visions of strutting into your office in nothing but a trenchcoat?’” Yikes. Photo Credit: Ed Yourdon
    Top Secret
  • Top Secret

    One day, Claire McDonald, a girl in the U.K., looked at her inbox and found a message from none other than the Pentagon with confidential information. She decided to reply to the message to let the Pentagon know its mistake, but that didn’t make much of a difference. According to the BBC, “[T]he e-mails kept coming, from the Pentagon, the Ministry of Defence and elsewhere. One detailed communications problems on British warships; another New Zealand's defence strategy. On average 11 such e-mails arrived a day for six months - so many that Claire's computer crashed, unable to cope with the huge file sizes.” Eventually, it was discovered that the an officer in the Royal Navy had made a typo and included the girl on their mailing list. Photo Credit: Marcin Wichary
    Targeting Job Seekers
  • Targeting Job Seekers

    You don’t have to be working a regular office job to be subject to bad e-mails. In fact, you don’t have to be working at all. As we reported recently, some Americans have reported being spammed with fake job offers. That might sound harmless enough until you think about how many Americans are also desperately seeking jobs in this economy. One e-mail from a company called DBP Execusearch read: “Are you still in the market? We felt your resume indicated that we may have immediate openings at DBP that could be right for you. However, if you are interested, we need some added information.” The message was also filled with dubious links and was really just phishing for personal information. Come on spammers, use some good taste at least. Photo Credit: Photomish Dan
    Services to Help You Deal With This Problem
  • Services to Help You Deal With This Problem

    Luckily, there are some tricks now to avoid making some of these e-mail gaffes. Google has introduced several features including special “Mail Goggles,” a series of simple questions, to ensure that you are not drunk or out of your mind when sending an e-mail. Ultimately though, nothing can protect you against your own poor judgment. When in doubt, don’t press send. As PC Magazine noted back in 2002, you’re always better off pressing cancel and writing the e-mail over to avoid mistakes. Not much has changed in the years since then. In fact, if the above examples indicate anything, it’s that we’re actually getting worse. Photo Credit: wetwebwork
  • Tweet Alongside Us

    Wait! If you haven't already, now is a great time to follow us on Twitter. You'll get all of our most important stories, right as they publish. Follow us: twitter.com/mainstr Photo Credit: Mixy
Show Comments