The Unavoidable Rules of the Internet

10 Most Unfortunate E-mails

A Bit Much
While it's acceptable to flirt over e-mail, there's a limit, and Joseph Dobbie went flying past it. In 2006, Dobbie met a woman at a barbecue and sent her a message after to ask her out for coffee. But he continued on, saying things like "Your smile is the freshest of my special memories. I will keep it with me for moments when I need to find a smile of my own." She thought it was over the top, forwarded it to her sister, who sent it on, and you know the rest. Dobbie was unfazed however, telling the press he'd received hundreds of romantic proposals.

The Breakup
As we've said, ending a relationship over e-mail is a bad way to go, but in 2003, Paul Kelly Tripplehorn, Jr. took it to another level. An intern for Texas Senator Kay Bailey Hutchison, Tripplehorn sent a vicious breakup letter to his now ex-girlfriend Michele, capping it with a signature that read, "your intellectual, moral, social, and emotional superior." The e-mail was sent all over, and Tripplehorn was fired. He later expressed deep regret over the incident and tragically committed suicide last fall.

CHUNG
In 2001, Peter Chung, a young Princeton grad who recently started a banking job in South Korea, sent an email to some former coworkers that ended up getting forwarded to millions. Rather than just let them know how he was doing, the banker, who referred to himself in the third person as CHUNG, bragged about going to clubs, getting phone numbers, and needing more condoms because he'd sleep with every woman in the country. The e-mail was forwarded around Wall Street, got back to his bosses, and he got canned.

The Dish
This e-mail from a woman describing her date in completely materialistic terms should strike a chord with anyone who's frustrated with the upper crust these days. Jacqueline Kim's e-mail to friends grading most parts of her date with Casey O'Brien, which she titled "The Dish," hit the Internet because of its emphasis on his money and looks. It's difficult to pinpoint the most vapid moment, but we'll go with her describing his boat, which only sat six people. Kim's phone number was included in the email, subjecting her to a bevy of fun calls.

Insensitive Much?
Revenge against a crappy boss is a joy few of us ever get to experience, but secretary Jenny Amner did just that by CC'ing a few coworkers in a mean exchange. Her boss, Richard Phillips, a high-salaried senior associate at the world's biggest law firm, Baker & McKenzie, e-mailed Amner to ask for £4 for dry cleaning costs after she accidentally spilled ketchup on his pants -- while she was away at her mother's funeral. She replied to the e-mail, copying 250 other employees on it, and said "I must apologise for not getting back to you straight away but due to my mother's sudden illness, death and funeral I have more pressing issues than your £4." The e-mail was forwarded out from there, and Phillips ended up leaving his job. Beautiful.

Layoffs
One of the worst parts about working for a struggling company is not knowing if your job is safe. Even worse is when an HR exec accidentally sends out a company-wide e-mail sends that was supposed to tell senior management how to handle impending layoffs, so not only did people know there would be firings, they knew how they would happen. This all happened last September at media agency Carat. As AdAge published portions of the email, it was clear that this was definitely not for the common worker's eyes. Oops.

The Hollywood Madam
Last August, the head of a high class prostitution ring in Los Angeles accidentally CC'd almost 50 clients in an e-mail that was supposed to go to only one client. While the names have never been released, Scandalist alleged that the list included a movie producer, club owners, a politician, a major sports team owner, and a prince. We imagine it must have been a nervous few weeks for them.

Best Party Ever
In 2006, Lucy Gao, a Citigroup intern, sent out an e-mail to 39 friends regarding her upcoming 21st birthday at a fancy hotel. That's usually fine, except Gao felt the need to detail her guests' behavior down to what they could wear, what exactly they should say to hotel staff, and when she would be accepting presents. Her coworkers forwarded it and it hit the press, which led Gao to say it was a joke that had gotten out of control. Her coworkers thought otherwise, but she kept her job.

The Worst
22-year-old banking clerk Trevor Luxton sent an e-mail to friends about having an encounter with a woman while talking to his girlfriend on the phone. He braggingly recounted the tale and asked whether he was the "worst boyfriend in the world or what?" At least one of the friends decided to share it with others and it seemed most people thought he was the worst. One person who didn't, however, was the girlfriend, who apparently accepted his marriage proposal.

Yummy?
An exchange between Claire Swire and her boyfriend became one of the first repeatedly forwarded e-mail blunders. What happened was the boyfriend sent Swire a joke about oral sex, to which she replied that his semen was particularly "yum" and made for great hair conditioner. The boyfriend proudly forwarded the exchange to some colleagues, who then did the same, resulting in a public shaming for both. There's some question to the validity of the whole thing, probably raised by Swire and the boyfriend themselves, but it seems legit.