Think twice, click once. It’s something you hear said in hindsight after some sort of monumental fallout occurs when someone has posted something awful on social media or, because we’re all about email here, sent a message that they probably would’ve been better off not sending.

So consider this a PSA of sorts as we show you some folks who probably got a quick lesson in sending apology emails.

3. Holly Leam-Taylor


We’ve all been there: You’re new to your job and trying to go that extra mile to seem super awesome and totally cool. Maybe bringing in that burnt loaf of pumpkin bread didn’t do the trick. Or the one and only time you were ever invited to lunch with colleagues, you ordered the table shots of warm, cheap tequila didn’t either. Who knows? Maybe people are just squares, man!


Cue the music for Holly Leam-Taylor, who in 2009 thought sending an email (above) to some of her colleagues with categories such as Boy Most Likely To Sleep His Way To The Top “… would be a good idea. Just a bit of fun.” And because this is the Internet and nobody knows what discretion is anymore, the email ended up being forwarded outside the office. And then it ended up being sent around the entire planet.


Within 24 hours, Leam-Taylor had resigned from her position in the company leaving us all to wonder which girl won the award for most hilariously/embarrassing office moment.

2. The Pentagonpentheader

Imagine back to your more formative years when you’d come in from a long day of playing kickball or Pogs or rollerblading to hop on AOL to see if your school crush responded to your email pouring your heart out to them.

Why did tell her about my blankie? Stupid, stupid, stupid.

But instead you see that your inbox is overflowing with top secret information, sent directly to you from a government agency. That’s precisely what happened to Claire McDonald in 2003. Coming in to check her email, McDonald found messages in her inbox from an individual in the Pentagon. When she replied back to point out the error: nothing. The messages kept coming until her computer crashed from all the top secret files she was getting.


1. United Airlines


Okay, so this next one isn’t an email, we get that. But it still bears mentioning because this could just as easily happen with an email, especially for those brands that have stock messages they send out.

Apparently, one reddit user had a not great experience with United Airlines and decided to voice their complaint. Fortunately, they did receive an apology. Unfortunately, the apology was less than personable.

"Also, (CUSTOMER NAME), do you want to grab a beer or something?"

Once posted to reddit, the letter went viral, causing the 2012 winner of Airline Quality Rating Report’s worst in the business award to respond with a shrug and say “Eh, it happens.”

Keep on, keeping on, United.