“Uh-Oh, Wrong Way!”: Tales Of Awkward ‘Oops’ Messages

Modern technology is very accessible to most people. However, for some, it’s not that easy to navigate. For years, sending and receiving messages became more convenient through using of cell phones. However, mistakes are inevitable.

Have you ever experienced accidentally sending the most horrendous message to someone? Well, these people went through the most embarrassing moments of their lives due to that. If these happened to you, what would you do?

1. Worst Error

We use Jabber messaging at work, and a co-worker was writing about a new anime he was watching. The little thing that pops up on the bottom right tells you when someone sent you a message.

I clicked it and typed, "Shut up, fool, nobody cares," ENTER. As it turns out, the chat app didn't feel like switching to my co-worker's chat window.

The afore-mentioned response was sent to a government official, who was one of our customers and was explaining to me a problem he was having with one of our programs.

I apologized and told him that that response was meant for someone else, and he said, "That's what I thought." This incident happened months ago, and I'm still working with this guy.

orgulodfan82

2. Naughty Dinner

My wife sent me a text message asking what I wanted for dinner. I had forgotten that we were having the family over for dinner that night.

I sent her a pic of my gentleman's veggies and asked her if she wanted that for dinner. I sent it to her entire family because I neglected to see it was a group text.

I thought about driving into oncoming traffic that night on my way home from work. That was a long night and the most embarrassing moment of my whole existence.

R1CHARDCRANIUM

3. Two Conversations

Happened just this past Sunday, actually. I was sending flirtatious texts back and forth with a girl, and in the middle of it, my mom started texting me.

She talked about some rare lizard she found in her backyard. Anyway, at some point, while going back and forth between texting the two, I accidentally texted my mom.

Well, no big deal, right? Uhh, certainly a BIG DEAL!!! Because I sent her, "I want you so bad right now. Get your arse over here." Yeah, it's awkward.

HorseMeatSandwich

4. Certainly An Accident

I texted a YouTube video of a guy doing One-armed push-ups to my boss, who lost his arm in a biking accident. That was a big oops moment for me!

It was supposed to go to my girlfriend (now fiancée). He was a good sport about it - he said, "Well, I'm going to have to try that out, thanks."

He laughed about it for a while and said that everybody had always avoided talking about his arm. Great guy. Just to add, he also ran a half marathon with my fiancée and me. He's a rockstar.

PrinceOfShapeir

5. Vanished Friendship

A few months back, my wife and I were going out to dinner with a few of her friends. The night before, a very dear friend of mine gave birth to twins and was still in the hospital.

I'd congratulated her earlier that morning. I got home that evening before my wife and decided to text my wife and ask her what she was wearing to the dinner to see how nice I needed to dress.

I did not check the name of the person I was texting because I usually talk to my wife more than anyone else. My friend called me laughing, asking why I wanted to know what she was wearing.

She claimed that, though hospital gowns leave little to the imagination, they certainly aren't sexy. To make matters worse, her husband is already threatened by our friendship. He was the first to read the text. Sadly, we haven't really spoken since.

xt0m1c

6. Sudden Revelation

I got kicked out of a nightclub for being what the bouncers deemed 'too drunk.' Anyway, in the face of such injustice, I went to text my friend.

Although it wasn't as grammatically correct at the time, the text pretty much said: "The heck, I can't believe they kicked me out! That girl wanted my private part."

I went to send it to my friend 'Mark' who is dangerously close to 'Mum' in my contact list. Yep, I bet you know what happened. I texted her the next day, saying I gave my phone to a friend to use because his was broken, but we both knew.

[deleted]

7. My Girlfriend’s Mom

"Diarrhea and it literally smells like a corpse. It looks yellow and doesn't seem to have anything floating in it." To my mother-in-law. Of a month.

I hadn't met in person yet, but I had her number from my girlfriend to wish her a happy birthday (it'll give a good impression).

Why did I send this to her? I was ill and had belly aches. My girlfriend is an ER nurse, and she asked me how my bowel movement was.  

Both their names start with the same letters. I actually got a reply. She told me to contact her girlfriend’s name. She would know what to do.

[deleted]

8. Good Error

I was really into a girl in college. She was in and out of a relationship with some dude at the time. We were hanging out one night, and her dude was being a jerkward.

Long story short, she ended up staying at my place that night. I didn't make a move, though, because I was not trying to be a rebound.

She got up early and left for work, and I woke up later to a text from a friend asking how it went. "I'm really into her, but she's wrapped up with some other dude, and I’m not trying to be a rebound."

And you guessed it, I sent it to the girl. I was so nervous at that time, and it was too embarrassing. Well, we got married 2 weeks ago.

rickayyy

9. App Abnormalities

My buddy was messaging me about how he was hesitant to use a Chinese launcher for Android because they could be stealing secrets.

I responded with, "I'm in ur fone stealing ur noodz!" It turns out that my messaging app screwed up and rearranged the latest entries when I hit the conversation for him.

Lo and behold, it was sent to my female coworker (this was also at 2 am). We did not speak for many months. That was too awkward, man.

gekkou

10. Believable Excuse

"How does your lady part feel, baby?" - Sent to my stepsister at 2 am, meant for my girlfriend at the time. This was a big deal because I came from a strict, until-marriage family.

I covered with, "OMG, I'M SO SORRY! That was meant for a male friend's name - I shot him yesterday in the bird paintballing!" Her response was, "OMG, THAT’S SOOOO FUNNY! Tell him I said hi!"  

She had to have known, but my story checked out because I had been paintballing the day prior, and I texted my friend telling him to update his Facebook, saying that his bird hurt from where I shot him. He did.

[deleted]

11. Same Name

I was flirting via text with a guy I'll call Dave. He asked for a revealing picture, and being a bit of an exhibitionist, I agreed to send him a shot of my lady parts.

I said I'd send it over WhatsApp, which we hadn't talked about before. Went onto the app, found his name in my contacts, and sent the lovely pic.

I have TWO Daves in my contacts. One of them is my colleague. I sent it to the wrong one. I just thought that was too much for me. I thought of resigning.

nitacla

12. New Owner

I texted a picture of my cat pooping in the litter box next to me, pooping on the toilet to my fiancée's old number. Yeah, this is no biggie for us.

We called the number a few hours later to see if someone else had it. Some thug-sounding guy answered the phone. There comes the ‘oops’ moment.  

So I could just imagine how confused Tyrone must have been getting a text of a white guy taking a poo with a cat also taking a dump.

Nightzel

13. Caught Lying

My boss called me to discuss a rumor she heard about herself. She thought I spread it because another co-worker told her I did.

I assured her I would never spend company time talking about her. I considered her a friend and valued her for my learning at the company.

We got off the phone, and I immediately rehashed the whole conversation for a friend at the company and sent it right to my boss.  

She sent back so much for not gossiping... Oops. I didn't lose my job, but it was tense for a few weeks. I cannot blame her. It was on me.

pokerchick86

14. Literally A Professional

Right after I graduated high school, my boyfriend and my high school science teacher had the same first names. What are the odds?

I accidentally emailed my science teacher a topless picture of me that was obviously meant for my boyfriend. My teacher responded with a simple email.

He stated, "Pretty sure this was not meant for me. Be more careful next time!" I guess he was really a professional. But that was soooo darn awkward.

dizzylizzy20

15. Ninja Moves

One night, I was drunk texting a girl I was planning on banging, and the message was pretty raunchy. I didn't get a response back for a little while and realized I had sent the message to my dad.

At first, I panicked but then remembered it was 1 am and figured Dad was asleep. I left the party immediately to go to my parent's house.

I snuck into my dad’s room (the two dogs on the bed didn't move at all, thank god) happily to see that his phone was blinking with an unread message. I took his phone and deleted my text.

Hobbiet

16. Roommate’s Judgement

I was in a long-distance relationship for about a week till I transferred to the same college as my girlfriend. We were texting, and she was saying something about how she couldn't wait to see me.

I replied, "Baby, I'm coming right now." My roommate on the bunk above me hears his phone buzz on his desk and gets down to check it.  

After looking at the text, he gave me the most disgusted/confused look and told me to wait until he was out of the room next time.

Lj_glass

17. Wrong Idea

I worked at a farm, and one day, I had to put down a very sick cow that couldn't walk and remove the body from the entrance to the milking parlor.

So I put it down and texted my boss, "Hey man, it's done. How do I get rid of the body?" He texts back, "What's done? What body? Is this a joke?"

I'm getting a little frustrated cuz my boss is older, and sometimes things slip his mind. 

Plus, a dead cow sitting out in the hot sun starts smelling pretty fast, so I text him, "Come on man, you know it's not a joke, now please just tell me how to get rid of the body. It's starting to smell."

He texts, "Um... Idk, you should probably go to the police." That's when I said WTF and checked who I was texting. It turns out it wasn't my boss.

It was one of my buddies. He was all freaked out, and I had to call him up to explain the situation. It's funny the guy still gives me a half-scared look every time I see him.

ILikeToSmokeWeedAlot

18. Messed Up Messing Around

Several years ago, on my birthday, my Grandfather sent me a Happy Birthday text. I was sitting in front of my girlfriend at the time and typed out "Where’s my money, WITCH?" in the reply section.

I swear I don’t intend to not actually hit send. I showed it to her, and we giggled. I accidentally hit the send button before I could erase the message and type a new one.  

I crapped diamonds for about 15 minutes, then joked my way out of it with him. I was surprised he was such a good sport about it.

Aewosme

19. Private Emojis

I had a client I was making some dresses for, and I'd been texting her back & forth about some little last-minute details regarding her order as I am a professional.

I'd also been texting my husband little naughty emoji scenes. Anyways, I made this elaborate bukkake emoji using the little smiley faces & some other crap & hit "send."

I watched & waited to see his reaction, but his phone didn't make the little noise associated with a text message. So I checked my phone & that's when I saw it.

I had sent this crap to a middle-aged woman who was having me make dresses for her kids! I texted her and apologized, and she was cool about it.

But when she came to pick up her order, you could tell that she wanted to get the heck out of there ASAP. I was so embarrassed when it happened I thought I was going to throw up. Now I'm extra careful when texting porn emojis.

AsshatMcBallsasaggin

20. Near Death Experience

This one was potentially terrifying. A classmate and I had the same advisor for student teaching, and the advisor was a real stickler and very strict about certain annoying things.

We really didn't like her and would often complain about her to one another through text messages. 

After a particularly bad experience with the advisor, I sent a text message that went something like, "Screw (advisor's name)."

After hitting send, I realized with horror that I had sent it to the number I had for my advisor. After a time of sheer terror, I got a message back saying that the message was undeliverable. Thankfully, the number I had was the advisor's landline number. Phew.

acydetchx

21. One Time Big Time

So, my best bud has a funny habit of texting me "aaaaah" whenever he decides to take a bathroom break at work. Every once in a while, I respond in kind.

Well, I decided this morning would be a good time to email him, "Just had an amazing poo. Thought you should know." I swear that was only one time.

However, I accidentally sent this to a different contact with the same first name, who happens to be the lead game designer at a local company where I interviewed a couple of years ago.

Tavataar

22. Worst Boss

Had a "boss" once who had no clue what he was doing and was always hitting on me and talking bad about my now husband. It was horrible.

One night at work, he was being really obnoxious, so I sent a ranting text to a friend. Nope, he got the text while standing right in front of me.

I completely owned it and told him how much I didn't like him or anything he did. He quit a few weeks later and went back to working as a janitor in another town. Screw him.

GeorgiaRomero

23. Close Call

"How many fingers are you using?" I was texting two different girls at the same time. This got sent to my ex, who I wanted to start dating again.

It was supposed to be sent to the girl I was messing around with who wanted me to text her dirty while I was working. It was pretty embarrassing.

My next reply was, "OMG! OMG! That probably sounded horrible out of context." I used this to buy me a short amount of time.  

Then, I responded with, "My buddy (enter name) just bought a compound bow and was seeing if he was using 2 or 3 fingers to pull it back." Luckily, she believed it and just laughed it off.

Ikeelu

24. New User

Upgraded to my first smartphone and didn't realize when you reply to a message, it now replies to everyone that message was sent to.

My friend sends me a group text saying, "This is ____. This is my new number. Save it." I respond, "Screw you and your god-darn new number!"

Then, I noticed that the message had other people's names in the preview. So I opened the message up again and said, "I think this just replied to everyone... Jesus!"

Then I was sure it was sent to everyone because a mutual friend texted me laughing about it... then my friend called me and was giving me crap about it and let me know that one of the people I replied to was his preacher.

7m7uf

25. Worst Last Date

I really messed up. I was moving out of my college town back to my hometown and was going on a last date with a girl I'd just met for the heck of it.

Right before I was about to leave, I was responding to a 'what's up' text from a friend and replied, 'getting my last arse in Bloomington' (it was meant to be funny ish; I’m not that big of a douche, at least I try not to be).

Well. I sent it to the girl. We still went out, but I explained that it meant it in jest with a buddy, and she, being a good sport, laughed it off with a head shake, 'boys.' Certainly, no arse was had that night, but we still had fun.

balfazahr

26. First Conversation

Kind of the opposite, but my now girlfriend of two years definitely sent me a text that I wasn't supposed to receive the first day we chatted.

It was about three in the morning, and I received a text from the girl I had started chatting with. It said something along the lines of 'I'm wasted and getting a boopy call!'

I responded by saying, 'What and who is this?' and she responded, 'Oops.' A little while after, I got another message asking me to come over, and I responded with, 'Naw, just rub one out and go to bed.'

I forgot what she responded with, but I just went back to sleep. Anyway, we eventually started dating, and about six months in, I found out that the message was meant for her best friend.

She said that she actually had a guy show up around three thirty in the morning. We have a pretty damn awesome relationship and have done a ton of stuff.

We have even more in the works, but this still bothers me endlessly. I'm not quite sure how to let go, and it's definitely something I either wish she hadn't done or that I knew of. We weren't together or anything so I can't really hold it against her.

Ghanni

27. Grounded Girl

I feel like this counts, but I was hooking up with a girl that I worked with. Every month, every employee had to do at least one weekend of overnight.

This was my weekend. I was asking her to stay and work. I went downstairs to get changed and texted her, "If you stay, we can make out in the changing room downstairs."

Within a minute, I got a call from her phone... Her mother had taken it away from her because she was grounded. Her mom was a very good family friend.  

She told me that it was very inappropriate and that she didn't want me to do it again. Here's the twist: her mom ended up being the person my dad cheated on my mom with. YOU TELL ME WHO'S INAPPROPRIATE!

unlimitednights

28. Worse Issue

I was in high school, and the guy I was dating had just dumped me. I texted my best friend, telling her that he wanted to leave me, and I was pretty head over heels at the time.

I was begging her to talk to him and figure out a way for me to get him back. I sent it to him instead. It was super awkward, and he was a total jerk about it.

But it got to my best friend anyway. Come to find out, she was there. He was leaving me to be with her. What are the odds? What a good friend she was.

octoberraine

29. Before D-day

Drunk texting for the win! I was out at a bachelorette weekend at a motel by the beach. We got pretty drunk, and we decided to go skinny dipping.

So I texted my fiance to let him know what we were doing and later sent him some spicy photos of goods by the motel pool. What a bright idea!

He never responded to my texts that night, and I called him the next day to chew him out. He said he never got my texts. Uh, why??  

Because it was my dad, I texted, not my fiance. It took me three weeks to get the courage up to ask my dad if he got texts from me last night. He said, “Yeah, let's never talk about that.” And we haven't!

nealesa

30. Unwanted Come Back

I dated a girl for a few years in high school who eventually ended up being crazy, tried to run me over with her car, broke into my online banking, etc.

Nothing too outrageous. A year after we split, I mistakenly sent a text meant for my mother, whose number differed from my ex's: "I love you and miss you. How have you been?"

Well, it turned into a hookup with the crazy ex who ended up pregnant, and now I have a beautiful son and an ex who spends child support on tattoos.

XaviXavi

31. Other Way Around

I was at a party with my male roommate (who is always very kind and protective), and there was a friend of mine there who was ALWAYS creepy and hitting on me.

The creepy friend was sitting next to me, trying to get in my pants, and I sent the text, "OH my gosh, he is creeping me out so bad. PLEASE SAVE ME!"

I thought I had sent it to my roommate, who would have gotten me out of there in an instant, but instead, I sent it to the Creepy friend.  

I then spent the rest of the evening with the creep being even more attentive to me, trying to "Protect me" from whoever was hitting on me.

scarlettlovescats

32. Sent To Everyone

Here it goes. I had a group assignment in college, and we had a group text about where to meet, each person's responsibilities, etc.

Well, the night before, my buddy and I had endeavored to eat a dozen lava wings a piece. He texted me the next day to ask me how I was feeling.

I replied with something along the lines of, "Great, except I feel like I was kicked in the gut by Bruce Lee, and I can crap through a screened door right now. Oh, and it feels like battery acid flowing from my arse."

Only I didn't reply to him, it was to the group. That really sucks, wish I could just vanish. Interestingly, no one ever replied or brought it up.

reddit_beats_college

33. Name Issues

I've been dating a girl named Angel. Who is simply on my phone as Angel. And we're really into each other physically. Put simply, she's a sick little thing in the sack and loves sending and receiving dirty texts.

Message from me upon waking the morning after she'd come over for some fun: "God darn, girl, I had to rub one out in the shower thanks to memories of you."

Of course, this went to another friend altogether. Same first name. Someone I like as a friend and have for years but have never been romantically interested in.  

Response text: "Wow. That's cool, but I don't think [her husband] would approve."

Me: "ABORT ABORT WRONG RECIPIENT"

[deleted]

34. Party Pooper

So, I had been invited to a friend's ( let's call him Bob ) surprise birthday party by his mother. He was turning 18.

I wanted to plan to carpool there with some friends, so I sent a text message to my friend, Marc, to ask him when he planned to leave his house to go there.

Well, you guess what happened? Since I typed, "When are you leaving for Bob's party," I sent the text message to.... Bob.

Realizing my mistake, I immediately called Bob and found myself talking to his voicemail and saying, "Haha, I guess you read the text message. Nice joke, heh? Hmm, well, cya later."

Of course, there was no way in hell he would believe I sent that as a joke, but I had to try anyway. Long story short, I went there, and he played it as if it was a big surprise.

I apologize to him profusely. He didn't talk about it to anyone else and is cool with it now. We're still friends to this day :)

come_2_daddy

35. Living Witness

My mom sent a group text (while away from the house on travel) with a picture of the 49ers cheerleaders practicing near where she was working with the caption, "Some of my coworkers are having trouble focusing."

My dad responded to this (and his phone text automatically replies to all) with a comment about how grainy the image got when you zoomed in.

They continued texting back and forth, accidentally cc-ing me, and bad puns led to flirty texts. Finally, I decided to text them to stop hitting reply all.

I know it was an embarrassing thing to acknowledge, but it may have saved me a rather scarring experience if it kept going.

CrossCheckPanda

36. Unknown Girl

I was doing the live recording for a music festival in San Francisco. I would be on-site at the event for roughly 12 hours per day, go out for a few drinks after to schmooze with the corporate peeps and unwind, then go home and mix a song completely exhausted/buzzed in the middle of the night.

I woke up to 2 text messages the next morning. The first one was from a friend, and one was from one of the people running the event.

A very sweet and young girl I didn't know at all. I forget what my friend sent me, but I responded, "Wait until you see my birdy." But guess who it went to?

420ANUSTART

37. Innocent Daughter

I sent a text to my dad that was meant for my boyfriend. It was...dirty. This is what happens when you date someone who shares a name with a parent.

Thankfully, I was at my parents' house, and I managed to grab my dad's phone and delete the message. I'd really like him to continue to view me as his innocent little girl.

I'd also like him to like my BF, and that wouldn't have helped. I have since put my BF in my phone under his nickname. I won't be making that mistake again.

[deleted]

38. The Advice

A woman I work with husband's name is John, and one of the sales reps' name is Joel. Before becoming a family man, I was known at work as a bit of an experienced guy.

So when (let's call her Beth) Beth started her romantic peak, but her husband was lagging, she turned to me for advice as I'm not the creepy, pervy kind.

I advise her to text him normally throughout the day, but the closer it gets to him coming home, the spicier. Guys like a build-up up, too.

So she's texting hubby all day, but she's shy. She eventually gets the nerve up at the end of the day to get her front lady part out in the loo and take a pic.

In her rush and embarrassment, she hit J and sent. Now, alphabetically, Joel comes first. Poor woman sent her massive mammaries (talking G cups here) to a guy she has to work closely with every day.

She came crying to me about it, so I went and talked to Joel. I explained it and asked if he'd seen the message, and he played it like a champ.

He said he left his phone in the car. He gave me the keys to give her so she could go delete it. It doesn't end there. As she opened the phone, he came barrelling out the door yelling, but it was too late.

His last action was taking a picture of his (tiny) schlong for his fiancée. Beth quickly exits and deletes her ta-tas, and Joel leaves the following week.

Timesharehandgun

39. Double Trouble

I have a friend, Danielle (Dan on my phone), and we mess with each other's names all the time. I was bored so I sent him, "YOU WITCH!"

Dan and Dad are right next to each other in the contacts. I did goof. He replied, "What?" and I freaked the fudge out, so I just said I was sorry and that it was for someone else.

So I typed a message to Dan that went something like, "OH CRAP, DAN, I JUST SENT "YOU WITCH" TO MY DAD, THINKING I SENT IT TO YOU." Guess who I sent it to? Yup. My father.

[deleted]

40. Grandma’s Nightmare

Oh God...I was at a party with my husband at a friend's house. We were drinking and playing Cards Against Humanity. I guess my grandma sent me a text without me realizing it.

We were all joking around, and I was texting my husband back and forth. You know, those funny in-the-same-room texts, and I don't remember the context.

But I accidentally sent "He wants your birdy" to my grandma. I played it off as someone stole my phone at the party and sent it. She never mentioned it again. Still mortifies me to this day.

raegunXD

41. Too Late

About five years ago, I was texting my girlfriend dirty things back and forth. My mother happened to text me asking something about dinner or whatnot.

I ignored it and got back to texting the girl... well... about a minute later, I got a text back from my mother saying, “What the heck did you just say... are you drunk?”

Then I responded, “What the hell are you talking about? No, I'm sober.” Mom replied, “Hahaha, look at the messages you sent.” And upon seeing it, I replied, “Jesus Christ, leave me the fudge alone.”

If you’re wondering what the message was, Well, "I can't wait to come over tonight so I can bang the heck out of you." Yep, I messed up.

Boston88

42. Busted Excuse

Not one I sent, but one I received. I got a text from my dad, clearly meant for his girlfriend, saying, "Love is waiting for you at home," to which I responded, "?"

Considering I don't live with my dad, this was confusing. He noticed his mistake and tried to save face with, "I just mean I love you, and you are always welcome here!"

So I let it go until he texted me again an hour later with, "So where are your kids going to be tonight?" I let him know he needs to find a way to better tell our names apart in his address book.

Toronto_Phil

43. Young Recipient

Sent a Snapchat to my friend Salvatore with the caption "Eat my craphole"... I got a Snapchat back from "Salvatore," which was a 14-year-old girl smiling, captioned, "Hi ;)"

I was mortified and angry. I still don't know why that little girl was on my Snapchat as my 21-year-old heavy-set Italian friend Sal (Prime Italian).

I texted Sal, asking if he got my Snapchat. He doesn't have one. Oh gosh, I just surely creeped out a kid!!! The NSA will get me soon enough.

MaybeNotStig

44. The Voice Message

The message wasn't embarrassing necessarily, but the situation was. This one night, my two other girlfriends and I are driving back from the bar. Friend 1, who I'm not very close to, was acting kind of standoffish the whole night.

For some reason, I thought it was a good idea to text this to Friend 2: "Friend 1 was neut very lively tanite huh?" The fact that I wrote it funny is important here because, well... I had forgotten an important detail about Friend 2's phone.

The touch screen was broken, and Siri, the iPhone's automated voice thing, read the message for her out loud. When I realized at the last minute that this was going to happen, I tried very pathetically to joke that she shouldn't check her text messages right away.  

She ended up playing it over and over again because she couldn't understand what Siri was saying (because of the weirdly spelled words).

Friend 1 knew right away what it was and said something like, "Omg, Salvis, are you freaking serious? You're such an airhead," and didn't talk for the rest of the drive home.

salvis

45. Secret Unveiled

We all had that friend in high school who secretly just got on everyone's nerves. One day, a bunch of us were hanging out, and this girl was being particularly sour.

Well, I went to text another friend, "Why is S being such a grump arse?" and sent it to said girl instead. I managed to beautifully pull it off.  

I made it look like I was being cute talking in the third person and concerned about her feelings. She never suspected. I was lucky.

KeysAndParrots