Message Sent: '20/20' Viewers' Email Mistakes

Nov. 9, 2012— -- The Undo command is a beautiful thing, but unfortunately it doesn't apply to one of the main tasks for which we use computers: sending email. Hit Reply All instead of Reply and your snarky gripe about the boss goes to the boss (and everyone else). Get lazy with Autofill and your intimate inside joke is enjoyed not by your sweetheart but Carl in Accounting.

"20/20" viewers know this painful realization only too well. Here's what they told us were some of their worst email blunder stories.

Watch the full story on the latest episode of "20/20" online HERE

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"I was looking for a job, and I wanted to learn Microsoft Word on the computer. So I was messing around with it one day, and my husband at the time was in the room, arguing with me. So I wrote "F--- YOU" really big in different colors and fonts, playing around, learning [the program]. I saved it under 'doc1.'

"A couple of days later, I completed my resume on Word and saved it as "res1." Well, I was talking to this woman about a job, and we hit it off. She said to send my resume, so I did. A day later she wrote back, "Same to you." I didn't know what that meant until I opened the attachment I sent her and realized I sent her 'doc1' instead of 'res1.'"

Teachable Moment

"Being a middle school teacher, I use email on a daily basis during the school year to communicate with parents. I'm very careful to use straightforward wording to avoid any misunderstandings or hurt feelings.

"One day a few years ago, I was cruising my personal email late one night and received a joke from a friend. You know the one, 'Deep inside there is a skinny me screaming to get out, but I can usually control the bitch with chocolate.'

"As I set in motion the Famous Forward I apparently hit the wrong contact. Seconds after hitting Send, I realized that I had clicked on the group that sends emails to ALL of my students' parents. I almost died, but there was no way to take it back. I immediately sent an apology email to those same parents and headed to bed to try to forget about my pending doom.

"The next morning I confessed my mistake to my principal just in case she received any complaints, then I braced myself as I opened my email for the first time since The Incident. To my surprise, I had several emails from parents thanking me for the good laugh, and absolutely NO complaints!

"I was shocked, but not as shocked as when a student walked into my classroom that morning with a gift bag full of chocolate and a cute note from her mom. What a relief it was to see that people really do still have a sense of humor, although I suspect some were laughing AT me instead of WITH me!"

What Meeting?

"In April 2012, I decided to email my children, nieces and nephews to plan a meeting to discuss family business with them. This was a very private meeting about their inheritance.

"In the process I typed in the email address of a family member who we absolutely did not want to know about our secret meeting. My heart skipped a beat when I saw her email address in the end. It was a devastating feeling of regrets."

Good to Know

"I keep my bills organized on an Excel spreadsheet, with links to each website, balance owed, date paid, login name and password so that I can conveniently pay each month. I thought it would be handy to have this at home, so I decided to email it to myself, and I could download it on my home computer.

"Instead, I accidentally emailed it to my entire email contact list -- business associates, customers, friends, family, everyone! I was mortified! Not only did everyone know the extent of my debt, but I had to manually go in and change each and every password, on each account.

"I got a few emails back along the lines of 'Thanks...good to know,' and also 'What the hell?' I eventually sent a mass reply back explaining my idiotic mistake."