5 Most Embarrassing Business Emails Ever Written

For well over 15 years now, email has been one of the primary methods of communicating online. Given how much we use it, it is not surprising that almost all of us have sent something stupid or embarrassing over email at one time or another. An average embarrassing email contains a misspelled word or something, but lucky for those of us who are entertained by other people’s faux pas (which is the vast majority of the internet users really), sometimes people really mess up, just check out the stories below.

Congratulations, You are Accepted

In 2009, the admissions office at the University of California in San Diego embarrassed the entire institution by accessing the incorrect database. As a result, an acceptance email was sent to the wrong list of freshman applicants. Luckily for them the list was not too long…oh wait, it contained 28,000 emails. The admissions office ended up sending apology letters, but nothing can mend a crushed dream.

Explicit Email Message to the Entire Student Body

In 2009, two employees at Cornell University sent steamy email messages to one another, full of sexually explicit details of their relationship. All was well until one of them accidentally sent the email correspondence to the entire student body at the Cornell Business School.  Of course, the email went viral (that was already a thing in 2009) and we are sure, became a cause of many awkward on-campus conversations. At least those two people were married…but quite inconveniently, not to each other.

Restroom Etiquette

This story is about Tom. Tom was a pig. Every time Tom used the bathroom at the office, he failed to flush the toilet, did not lift the seat prior to doing his business, and often missed the toilet when discarding used pieces of toilet paper. Tom needed to be told off. One of the employees stepped up and decided to give Tom a piece of mind in an email. In that message, the employee provided a detailed list of Tom’s ‘charming’ misdeeds. Completely reasonable (and completely disgusting), right? Unfortunately, the employee chose the wrong contact list and ended up emailing his detailed complaints to every potential customer the business had. We are sure that someone got fired, and it probably was not Tom.

The Unexpected Job Offer

Meet Mindy, she is a senior recruiter at a large corporation and she used to have an assistant - Jill (notice the used to have). Back in 2010, Mindy was on a task to fill a senior management position and it was not a piece of cake. Mindy has spent many weeks assembling a list of top 50 candidates and several more weeks were spent on conducting interviews. Finally, Mindy was almost done and the list was painstakingly distilled to only 5 absolute best manager hopefuls and then finally, the one was chosen.

Mindy finally had a chance to sit back and relax for a minute and asked Jill to send out a cookie-cutter congratulatory email that contained the job offer. Unfortunately, Jill messed up and sent the email to the wrong guy. He was so wrong, in fact, that he was never even one of the 5 finalists. And that was not the end of it.  When a letter of apology was sent, the candidate turned around and threatened legal action, which as any HR manager will tell you can really damage a company. As a result, the company was stuck having to hire the wrong candidate for the position. Undoubtedly, Mindy had to search for a new assistant soon thereafter.

Dirty Larry

It was 2002 and Larry could do no wrong. Being the most successful salesman at a sizeable company, he could do virtually anything and still keep his job. Like many men in 2002 (before the proliferation of online video streaming), Larry had a secret folder on his computer, full of dirty jokes and even dirtier pictures. We imagine that the folder title was something like ‘Hottest Deals’. Unlike many men however, Larry had a long list of prospects and clients, most of whom were conservative executives and government officials. You can already guess what happened…

One day, Larry was working on an email, with a subject line that said “Exceptional deals for my best customers!”. We can only imagine the look of horror on Larry’s face when he clicked ‘Send’ only to realize that the wrong folder was attached. Needless to say he had to start from scratch again, this time with a new company.

If there is a moral to all these stories, it’s undoubtedly this ‘read your email and check your attachment before sending it!’. Oh, and also, ‘don’t cheat on your significant other’ and ‘don’t store a dirty pics folder on your computer’.