Awkward AF Texts originally from R/AskReddit
1.
I meant to text my wife, but instead I texted my boss asking “have you ever held your shit in too long, and when you finally get to go, it hurts?”
He responded with “😂😂😂😂”.
2.
Sent a dick pic to a family group message. Intended for a lady friend whom requested, in the meantime my dad sent a message to me, my mom, sisters, and uncle. I took the pic went to the message on top (not my lady friend) hit send.
Realized a split second later but it was too late. I wrote something like ‘sorry guys didn’t mean to send that to you’, and got no response. Fucking mortified. Sometimes right before I am falling asleep I think of it and I can literally no longer sleep.
3.
I once accidentally sent my mom a video meant for my SO. I just called her up and told her that the video I sent her suggestive, meant for my SO and to please erase it. She did. And that was it.
4.
Texted my friend I’d call her back after I was done pooping but I ate White Castle the night before so it may be a good while. I even put the little poo emojis at the end of the text.
Sent it to the painter I had been corresponding with all day who was actually downstairs starting on the kitchen. I wanted to die.
5.
My husband got a text from a random guy telling his ex that if she didn’t let him see his kids he would kill himself in front of her.
6.
I got an accidental text from my girlfriend once saying “if things keep going this good [my name] and I, we will be married In a year”. I was going to break up with her that weekend.
7.
“Is that what you think I am, some guy who eats you out at the first opportunity?”
Sent that to my boss. Luckily we are good friends and she just teased me about it for a month or so after that. I meant to type “rats you out” but autocorrect had different plans for me…
8.
I sent “my wife” a text detailing a very specific sexual act I would like to perform on her.
Yup, sent it to my mom.
9.
Texted a guy who I just started dating saying “goodnight, love you” intended for my mum. It’s ok though he’s now my husband 😅
10.
I got a dickpick from my best friend, my name starts with the same letters as his GF’s do, the first 4 of the 5 that is.
11.
I had an asthma attack at school and didn’t have my inhaler. My teaching partner took over and I had to be taken by ambulance to the hospital.
My wife arrived and I was stabilized pretty quick. We were going to visit my parents that night, so my wife sent my mother a text….
“Christian had an asthma attack. They took him to the ER. He’s fine now.”….however, autocorrect changed it to “He’s gone now.”
12.
To Mom: Hey, care if I drop by and pick up another gram?
13.
I was talking to my mom about the birthday cake that I had ordered for my girlfriend’s party that evening. I finished telling her what flavor it was, and put my phone down. A minute later, I got a text saying “they diagnosed that his anal glands may have ruptured. There’s blood everywhere, and it may be cancerous.”
Needless to say, I had several questions after this. Turns out she meant to text my dad about her dog.
14.
I once emailed my boss two paragraphs telling him what an asshole he is. Meant to email my girlfriend.
He never mentioned a word of it.
15.
“Yeah? Well how about I cum in your e-cig and you vape that, huh?”
Meant for my wife. Sent to my mother. My very conservative, very religious mother who thinks I never swear despite ten years in the army.
16.
Received a dickpic from my 60 year old father. Received another one about a month later. He promptly texted “Please ignore” but the damage was done.
17.
I had an ex once that I am pretty sure wanted to try a golden shower and I used to tease her about it because she wouldn’t admit it. One day I read about how it’s actually the urine in the pool that makes your eyes red and not the chlorine.
I went to text her about it but accidentally replied to a group text with a bunch of acquaintances (~15 people) that I play poker with. The reason that group text was at the top of the list? Because the host had to cancel the game that weekend because his mom passed away. So among all the sorry’s and condolences, there’s my text about how getting red eyes in the pool is like getting pissed in the face.
18.
Got this text:
“Derrick I need anal”
Mind you my name is Nate
Edit* After I responded, the girl literally just called and said “Derrick stop fucking with me I know you like it you bastard”
19.
In highschool I stayed the night at my friend Jonah’s. My parents were very strict and I hadn’t told them my plans, so they texted me “Where are you. Tell me now”. My phone however, was at 1% and I needed to reply fast, so I texted “Jonahs” and my phone immediately died after sending.
It wasn’t until the morning when I recharged my phone and saw that it auto corrected “Jonahs” to “No Haha” along with a long list of angry replies from my parents
20.
Sent a text to my friend telling her that there was a girl that I wanted to sleep with and that I finally found a way to hang out with her. It was real braggy and whatnot…
Well I sent it to the girl I was talking about and her response was,”haha so that was your plan the whole time? I’m not feeling well maybe we can hang out some other time.”
I never talked to her again.
21.
I told my step-dad I couldn’t wait to suck his dick
It was meant for some guy I was hooking up with later that night
22.
My co-worker Karl was texting his wife one morning, after they’d had a little “Sexy time” before he left for work. Karl was driving to work at 8am, and wrote his wife a nasty “post-sexy time” recap saying what he liked so much about her giving him a blowjob and how he finished…. and how she was just his dirty little {expletive}.
WELL… the text message went out to a group chat, with most of Karl’s wife’s family… because they all were discussing family reunion plans.
He didn’t know what he’d done, happily driving to work during his refractory period, until his Father-in-Law was the first one to reply to Karl’s text message saying, “Good to hear you’re up taking care of business…”
The damage control was hysterical that entire day at work, Karl having hushed phone calls with his wife, and him explaining how her grandmother was texting her sex advice… so cringe worthy if it was me, but it wasn’t… so I laughed.
23.
Not me but two of my best friends that were dating, let’s call them Andrew and Christina. Andrew was on student exchange to another school for the semester and as all distance couples do, him and Christina were sending photos via text that mother would not approve of… and oh boy, she did not.
Christina’s families iPad had been receiving the full frontal texts and pictures, and when her mom saw them all, instantly replied with “STOP YOU IDIOTS STOP!!!!”
Since then, they got married, and all is well. However they no longer send dirty messages, and anyone lucky enough to hear this story never forgets “The family affair”.
24.
To my mom: “Can’t talk now, I’m in a classmate.”
25.
I once had a client who was a recent vet of Afghanistan or Iraq. He was about to start the same college program my sister was attending. I told him I would give her his contact info. Then he accidentally texted me “did u get anal?”
26.
“You better wash yo ass ’cause I’m on my way home and I want to eat it” from tipsy husband sent to group message with co-worker and myself.
27.
I texted an extremely attractive estate agent, and ended it with “thanks a lot”, but actually sent “thanks slut”, and only realised when she neglected to reply.
Our next meeting was somewhat cool despite my apology.
28.
My friend in high school accidentally sent something along the lines of “My Stepdad gives $5 blowjobs” to his stepdad (he used his real name in the text). It was meant to be some immature joke sent to one of his friends. The look of horror on his face when he realized who he had sent the text to was something I’ll never forget.
29.
Once my husband was having some digestive issues and he went upstairs to go to the bathroom. So I decided to tease him about it because I’m an asshole. I texted him “Hi lover, I hope you are having a good poop. Try not to prolapse” but I accidentally sent it to our very uptight female friend instead. She was unhappy.
30.
I wanted to send my friend a link to the rainbow six siege beta trailer because it was coming out the next day but ( without noticing ) sent him a porn link with the text “we’re doing this all day tomorrow” I had failed to copy the link and I had porn linked because sometimes safari stops loading so I copy a link so I can easily get back to what I was doing. The next day he thought I wrote that on purpose but I told him it wasn’t and we had a good laugh. Still the embarrassment was killing me.
31.
After telling my family I was an atheist, my sister sent a text, thinking it was to her best friend, that laid out how heartbroken she was about me not loving God any more. It was very insightful to read but so so fucking painful to know how much hurt she was going through.
32.
Called in sick to work because I was hung over — but told work I had a bad cold. Sent a text to my boss — who has the same first name as a friend I meant to text — talking about how hung over I was…
