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June 25, 2015
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After years of experimenting with "undo send" as a Labs feature, Google announced that it was officially adding it as an option for Gmail users. That's little help for all of the emails we've already sent that we wish we could unsent.

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After years of experimenting with “undo send” as a Labs feature, Google announced that it was officially adding it as an option for Gmail users. That’s little help for all of the emails we’ve already sent that we wish we could unsend, the damage those emails did that we wish we could undo. See below for seven emails sent to the wrong recipient, in each case the fatal error realized after the “Send” button was clicked.


Hello Mistress,

I need to think of a better nickname for you than “Mistress!” When I start to type “Mistress” in the “to” field, the email address for my wife “Melissa” comes up and it gives me a miniature heart attack. I’ll have to save you in my contacts as something else!

Oh dear, can you imagine if I sent an email to my wife that I meant to send to you, my mistress? The thought turns my stomach. I don’t even want to check the “to” field right now, the hypothetical is too much to bare!

At any rate, I’m enjoying this extramarital affair we’re having! Just emailing to make sure we’re still on for our usual Tuesday night tryst.

I’m looking forward to doing the things with you that my wife doesn’t let me to do her and/or do to me.

Hey Greg Courter,

Don’t you think that Greg Courtier is a real jerk? Funny how similar your names are, though. Anyway, just wanted to send you - Greg Courter - an email to let you know how I feel about our mutual acquaintance Greg Courtier.

Take care. Maybe see you at bowling on Thursday? (Hope the other Greg isn’t there - haha!)

Mr. Tablerson,

It might just be the momentary anger that I’m feeling after you reprimanded me in front of several of my co-workers for a mistake that right now seems trivial from my perspective but with the benefit of time and cooler emotions I might recognize was in fact an important matter for which your admonishment was completely called for and what I interpret now in this instant as meanness on your part for making me feel small could instead be interpreted at a moment not too far from now, say after drinking a glass of water and taking a walk around the parking lot, as perhaps not meanness but rather something almost like professional generosity in that it didn’t take the form of a formal sanction or dock in my pay, and whose public nature could be justified as potentially saving my coworkers the indignity of making a similar mistake in the future, and even now only 90 seconds later or so I realize that my memory of you “yelling” is probably my adrenaline fueled system mischaracterizing the actual event in my imperfect human memory (which is fallible, let’s not forget!) and at most your voice could be described as “stern”, not to mention the fact that you having to discipline your subordinates is probably equally or more unfun for you in terms of being one of the tasks you’re required as a part of your job role in our corporate hierarchy to do; all that being said, in this present moment I just wanted to dash off a quick email to say “Fuck off, asshole.”

Hey Greg Courtier,

Oops! Oh man am I embarrassed. I just realized I sent you an email that I meant to send Greg Courter and in it I said something not so nice about you (well, you saw it, let’s not beat around the bush: I called you a jerk. A real jerk, in fact).

I’d like to formally apologize and also add that, now that I think about it, the real real jerk is Greg Courter. Feels good to put that into writing for saving in the digital archive of my inbox.

Anyway, maybe see you at bowling Thursday? Please reply to this email before then - don’t want things to be awkward for the three of us.

Melissa,

Sweetheart, please won’t you return my calls? I know I messed up. I’m scum. You didn’t deserve to be cheated on, and to have to find out about it from me accidentally sending you an email that I meant to send to my mistress just adds insult to injury. If only those eggheads at Google would create an “undo send” feature and/or make it more well known that an experimental “undo send” feature has been widely available in the settings section since 2009. I don’t mean to pass the blame to Google, although I do think they are at least somewhat to blame for my marital indiscretion.

Would it make you feel better if I told you that my mistress means nothing to me? I don’t love her. She is trash compared to you. I love you so much and with my self-loathing issues (we’ve discussed them) it’s so hard for me to feel like I deserve you, so I slummed it with that mistress of mine. Blek! That’s how disgusted I am by the thought of her now - I type blek! in disgust. Even though she does thing to me and lets me do things to her that you do not, the truth is that I respect you for not doing those things which, to be honest, I think are just sort of gross and just wanted to try them because I saw them in a pornographic video online.

In fact, in my contacts I have her named saved as “Melissa? No, This Isn’t Melissa; This Woman Is My Inferior Mistress.” I just put “Melissa? No, This Isn’t Melissa” as her first name and “This Woman Is My Inferior Mistress” as her last name. So literally every time I send her an email, I have to type your name first! Doesn’t that mean something?

Mr. Tablerson,

[NOTE TO SELF: BE SURE TO SPELL CHECK THIS EMAIL BEFORE SENDING FROM DRAFTS. THAT ANAL RETENTIVE ASSHOLE MR. TABLERSON WON’T ACCEPT MY APOLOGY IF I MAKE A TYPO. ALSO, SMART OF ME TO SAVE THIS IN DRAFTS FIRST SO I DON’T ACCIDENTALLY SEND TO EARLY. WAIT, HOW DO I SAVE THIS AS A DRAFT AGAIN? I THINK I JUST HIT “SEND” AND THEN IT WILL GIVE ME THE OPTION “ARE YOU SURE YOU DON’T WANT TO SAVE AS A DRAFT INSTEAD?”, RIGHT? I GUESS I’LL STOP TYPING MY INTERNAL MONOLOGUE NOW AND GIVE THAT A TRY.]

Gregs,

I thought it was time that I got all three of us on an email. Look, I called you each a “real jerk.” But the truth is, I am the one who is a real jerk. You see, I keep typing up real stupid emails real fast and then hitting send without bothering to check that I’m sending them to the correct recipients. Melissa wants a divorce because I sent her an email that was meant for my mistress; my mistress is through with me because I sent her an email that was meant for my wife; and my boss fired me because I sent him an email that I probably shouldn’t have sent and another email that I sent before I meant to. In short, it’s been a bad day. If only sending emails could be undone. Alas, they cannot. What is sent is sent, moved from the outbox of mine to the inbox of another. These emails have been sent. Permanently and irrevocably sent.

Since I cannot undo, all I can do is ask the both of you, my two truest friends, to forgive. See you both at bowling on Thursday? Unrelated, can one of you give me a ride?

ps - I’ve attached something that I think will make everything OK, provided I don’t make any other slip-ups between now and hitting “send.”

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