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The Worst 'Reply-All' Email Disasters

Can you top my horrific tale? I doubt it.

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A graphic of a person bent embarrassed over their laptop as the people around them read a mistakenly sent reply all email.
Jade Schulz
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Two years ago, I received a distressed text from my best friend. “My life is over,” she wrote. “Check your email.” I opened my inbox to what I thought was a forwarded message from my BFF’s boss, telling her that the company was closing its doors and asking her not to spread the news until it was official. I followed the brief thread to learn that my friend’s boss and her business partner were parting ways, and my friend was being asked to relocate to a new city to help her boss set up a new shop. The part about keeping it all confidential was underlined and in bold. And my friend had replied with enthusiasm, saying that she would of course keep this news to herself while thanking him for the opportunity.

So I replied like a good friend. “I’m so sorry! Very smart of you to accept the opportunity and keep it on the back burner, even though I know the last thing you want to do is move away from your boyfriend.”

Except I didn’t reply. I replied-all. And it wasn’t a forward. It was a reply to her boss with my address in the Bcc field. In other words, her boss read every word I’d written and predictably, the opportunity to relocate was promptly rescinded.

This is my reply-all disaster tale. And I’m sure you have one, too.

Susan from Chicago was in a comedy improv group with a bunch of very funny people and one remarkably not-so-funny woman. “We all know these people,” says Susan. “They think they’re funny, they want to be funny, and like a cat taking a bath it’s simply painful to watch.”

The unfunny woman would email the rest of the group with a daily joke. And, you guessed it, the joke was never funny. So one day, a member of the group replied, “She can’t even find a funny joke!” — followed by a private email to Susan saying, “I just accidentally replied-all.”

“The poor girl never said a word about it,” says Susan. “But that was the end of the daily joke email.” Sounds like some reply-all stories have happy endings!

Even so, it’s important to use caution when replying to emails, and the same goes for text messaging.

Ellen from Boston was in the car with her parents on Yom Kippur, the Jewish Holy Day of Atonement. They were driving to temple for holiday services when Ellen’s mom said something annoying and Ellen texted her husband, “My mother is a moron.” Except she didn’t text her husband. She texted her mom, who promptly replied from the front seat, “I'm glad you think I'm a moron. I guess you can atone for it today.”

Even computers make reply-all snafus, as in 2009 when UC San Diego’s admissions department accidentally accepted 28,000 students who had their hopes dashed hours later by a second email rejecting them from the college.

Hopefully our office email systems have evolved since 2009, but human error always puts us at risk of developing digital foot-in-mouth disease. To avoid cyber-embarrassment (or causing some real hurt), follow a few simple rules before hitting send:

1. Think before you reply! Just like we tell our kids, everything you put out there on the internet is out there for the world to see, even if we think we’re being private. This goes for email, texting and social media.

2. Check your email settings for an “undo send” option. Gmail, for example, gives you up to 30 seconds to take it back after hitting send if you enable this feature.

3. If you reply to a forward of someone else’s email, remove the “.com” from email addresses in the forwarded header so the recipient of your email doesn’t accidentally reply to the wrong party.

4. Be wary of the group text! Make sure you are aware of everyone in the group, and if you don’t know who someone is, ask. Until you can assign an identity to every number on that text, don’t say anything you wouldn’t want the world to hear.