World's Worst E-Mail Gaffes, Read 'em and Reap Some Lessons

Nov. 16, 2009— -- There's a new contender for the worst e-mail gaffe of all time. Actually two.

John and Lisa, a pair of very married (not to each other) and very adulterous employees at Cornell University mistakenly sent a long and graphic e-mail string to a general e-mail list at the Johnson School at Cornell.

As a result, last week John and Lisa's 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?" You get the idea.

If John and Lisa, whose last names have mercifully been withheld, can take comfort in anything, it's that they are not alone.

The list of people who have humiliated and embarrassed themselves via e-mail is a long one, said Chas Newkey-Burden, author of "Great E-Mail Disasters," as he ticked off some examples. "There are so many stories of people who have just made complete idiots of themselves. In one way or another, everybody has done something stupid via e-mail."

In 2000, the Pentagon mistakenly included a school girl's e-mail address to a group list. Claire McDonald, and her parents, were surprised to see sensitive defense briefings showing up in her inbox.

After a trip to China, an aide to then-chancellor Gordon Brown sent out an e-mail that included advice on pulling the corners of your eyes back to "look Chinese." The racist e-mail was sent to dozens of journalists by mistake.

On Sept 11, 2001 a public relations executive e-mailed some colleagues after the Twin Towers fell with the following message: "This would be a good day to bury bad news."

Even Bill Gates, founder of Microsoft, got tripped up by e-mail. On the stand to testify in an anti-trust suit, Gates claimed he couldn't recall a number of important points related to his testimony. A check of his e-mail revealed that Gates' was actually far more involved in decisions about Microsoft than his testimony implied.

And who could forget poor old Joseph Dobbie who became known as the "Rambling Romeo."

According to Newkey-Burden, the Joe Dobbie story all started innocently enough. Dobbie briefly met a woman, Kate Winsall, at a party. Winsall passed him a piece of cake.

Two days later, Dobbie sat down to compose an 800-word over-the-top e-mail that read in part: "This is the part where I throw caution to the wind, the part where I listen to my heart and remember that I should live my life as an exultation and revel in the opportunity to try; the part where I refuse to apologize for who I am; the part where I trust that the lady I met on Saturday night is, as I suspect, able to see sincerity where others would see cliché.

"I am fortunate enough to have been able to collect a number of special memories. They are memories of moments that made any struggle leading up to them worthwhile -- your smile is the freshest of my special memories." And so on.

That 2006 e-mail was forwarded by Winsall to her sister and quickly went viral. Dobbie became such a household name that street vendors started selling Joe Dobbie t-shirts. Dobbie himself had to disconnect his phone.