16 Of The Most Mortifying Wrong Window Stories We’ve Ever Heard

16 Of The Most Mortifying Wrong Window Stories We’ve Ever Heard

Late last year, Giz US asked readers about their most embarrassing chat-related mistakes ever. From accidentally sexting your loved ones to chatting your dealer during a presentation, they delivered. Anything sound familiar to you guys? Have any of your own horror stories to share?

A female coworker of mine was iChatting with a brand new employee on another team. She intended to send him a screenshot of what she needed help with, but instead sent him this image that had been saved to her computer from a chat with a friend:

Luckily for everyone involved, the recipient had an amazing sense of humour about the whole thing! I believe his first response was something along the lines of “Well that’s rather forward of you!” – DaboGirl

I sent a full paragraph of pee fetish cybersex text to a girl I was interested in at the time over WoW. I played it off in what may or may not have been a smooth manner. I followed it up with something like “… is what someone just said in general chat lol this game is full of weirdos.” – Moonshadow Kati aka Lady Locksmith

My story’s from years ago at my first job at a production company in Los Angeles.

We’d just delivered a spot to a client and they kept emailing me for copies of the spot. I should have directed them to our production assistant but instead I forwarded their email to my boss with something like “When are we done with this stupid project? This dumbass keeps bugging me about dubs.”

I walked into my boss’s office a minute later and asked “did you get my email?”

He looked at his screen but didn’t see it.

“Refresh it or something. I just sent it.”

He did. Several times. Still nothing.

“Hang on. Maybe it didn’t send.” I walked back to my desk and looked at the “sent” messages. I pressed reply instead of forward and now the client had my email.

I ran back to my boss’s office and explained. I was sure I was going to be fired but he covered for me and talked to the client himself to say “Eric is kind of an idiot and keeps about 50 windows open on his computer. He was thinking of another client and, again, he’s an idiot. I’ll make sure you get those copies.”

The client seemed to buy it, I kept my job, and now I don’t send a work-related email without triple checking where it’s going first. So win/win/win?


Guy next to me was the recipient of this one (names and stuff redacted).

Team Live Badass

Had a Facebook chat with a friend up on my second screen, it had been open for days. On the main screen I was doing some. . . research*. . . and I accidentally typed my query into the Facebook chat.

I am so glad the FB messenger app lets you delete messages, cause I grabbed my phone and deleted it as fast as I could – I’m pretty sure he never saw it. If he did, he never mentioned it.

*Of an adult nature. . . – zeel

I chatted to what I thought was a friend that I had a huge crush on a coworker, jasper, but accidentally chatted jasper :/ – Meg Neal

A twofer, which I did not start, but did finish.

A woman I was training at work sent me by mistake an “I love you, [her husband’s name]”. Absentmindedly, I thought it was a message from my wife, who I was also texting at the time. Absentmindedly, I answered “I love you too”.

That became an interesting and awkward next workday. – Grive

This was my third week at a new job. My wife and I were e-mailing about a couple we met in our neighbourhood the night before. They were REALLY IN LOVE and were constantly involved with baby-talk and weird pet names (honey bunch, baby cakes, etc). My last response to my wife was “I wuv you, angel-tits!”

I had clicked on the wrong email and replied to every single person in my company.

You cannot will yourself to die.


I build websites for people… and one of my clients was a Catholic Church in Florida. Their site admin messages me for real quick things in Google Hangouts sometimes. Worth mentioning is the fabulousness of Google Hangouts’ way of handling GIF’s. I was enjoying “Bilbo Fucking Baggins”:

And I quickly decided it must be sent to a coworker. Except… it didn’t go to my coworker. It went to dear Father Tom in Florida. – chuckzee

Texting my ex-wife “I love you” when it was meant for my fiancé. – TomMikele

I had a bunch of gchats going, including ones with my cousin and my boyfriend, who have the same name. My boyfriend and I were long-distance so our gchats could get….spicy.

And that’s how I ended up sending my cousin a message about how we should totally do standing 69 the next time he was in town. – Kate Knibbs

I am in a fraternity at my college. We all like to talk smack to each other of course. One day we had a meeting with the entire chapter. The president asked to use my laptop to display his presentation, I said yes. I spent a good amount of the previous night sexting my long distance girlfriend. We use hangouts because we both have Android phones. Well, I also use hangouts on my laptop to text her throughout the day. As the president is going through his presentation I got a new hangouts message, initiating a popup on my screen. Keep in mind this is being projected in front my 100 of my best friends. And there it was in last message I sent was a picture of my penis, it was now on the screen in front of all my friends. – marcus

I just found the original gchat transcript and it hurts. I was iming Nick Stango about one of our coworkers (who isn’t here anymore), when I accidentally imed that coworker himself. After I realised what I’d done, I had to keep referring to him in the third person to try to save myself. I think maybe it just made it worse.

[I feel dead inside all over again/name’s changed to protect the innocent.]

Ashley Feinberg:

im so curious what kevin’s gf is like


what is your gf like

Kevin Fakename:

haha she’s super nice

Ashley Feinberg:

/how long have yall been dating

(im really bored if you cant tell) – Ashley Feinberg

Sitting on a con call with the new CEO one day and an audience of hundreds of pompous execs globally. I am running the Citrix meeting laptop, and my connection IM’s me that the new Kush was in and how much I wanted – so it comes up on my screen in the middle of this webinar, and visible to the whole board and leadership team. Needless to say the piss tester was in my office waiting for me with cup after the call. I just resigned and packed up my shit, went home and rolled a fat one. Gig over. – Nonhipster Austinite

I was simultaneously talking to my very pregnant (at the time) wife on IM, speaking on a conference call, and responding to an email from my CEO…while also playing one of those old school text based games. My mind was in a gajillion places at once.

Long story short, I sent my CEO a message saying “kill dwarf”…thankfully his admin was able to intercept and delete said message. – geekymitch

And then there was Heymanryan, who pointed out that a very high profile wrong window story was taking place this week online:

The World Health Organisation just did this yesterday by sending a message to BuzzFeed on accident stating they thought BuzzFeed was banned:http://mashable.com/2014/11/13/who…

There are plenty more terrible stories to be enjoyed

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