Every Halloween, we like to ask our employees and the Reddit community for their best texting horror stories. Here are our favorite horrifying, heartwarming and hilarious texting mishaps from 2018.

Horrifying

“I was walking home when I received a text from an unknown number saying, ‘You look good in that yellow dress.’ I was, in fact, wearing a yellow dress!”

“A friend at work got a text today from a guy she has turned down multiple times. The text said, ‘I’ve kept every voicemail from you since last January.’”

“My boss’s name was Miriam, right above Mom in my contact list. You can guess who I sent, ‘I hate my boss so much!’ to. I was mortified because I realized right away what I had done and locked myself in the bathroom. Minutes later, my boss came knocking on the door asking if I was okay. I was 16 and it was my first job!”

“I was somewhat flirting with a woman named Heather and she asked for a selfie of me. I took a picture (normal one) and accidentally sent it to Hector, my old manager I hadn’t talked to in years.”

“One time, my sister texted me instead of my mom. It was about my surprise birthday party that they’d planned for the next day. That one was a little disappointing.”

“My Mother-in-Law came to visit when I specifically requested her not to (I was really ill and not up to it). She began picking at me and generally making me miserable. I texted my other half that I wished she would leave and said I was tired of her interfering. Well, I realized I sent the text to Mother-in-Law by mistake as she sat two feet away from me on the other sofa. I heard her phone ping as I realized my horrifying mistake. Knowing she would react badly, I said, ‘Oh, that’s from me, I messaged you by accident,’ and told her I meant to send it to her son. Without looking, she handed me the phone and said, ‘Delete it.’ I felt truly awful, and it was a lucky escape. I’ve learned my lesson – now, I don’t talk ill of anyone anymore even if they deserve it. And I double check who I’m sending texts to!”

“On a business trip at my last job, I was going back and forth one evening with texts to my wife and a colleague (separate texts)…wife texted her final ‘Sweet dreams ????’ and I didn’t respond immediately, as I was multi-tasking. Finally, I responded back ‘Sweet dreams ????.’ Well, you guessed it…I sent my loving goodnight message to my colleague by accident instead of my wife. Of course, he laughed about it, but warned of a potential HR violation (in jest, of course). D’oh!”

“I am still really good friends with an ex, and I was chatting with him and my husband at the same time. I accidentally sent ‘I love you’ to my ex, but only realized my mistake a few minutes later and corrected myself. My ex said he spent those few minutes staring at his phone in horror!”

Heartwarming

“I texted my boyfriend’s mom asking for her ceviche recipe. She’s Peruvian, so I knew she’d have a great one. Shortly thereafter, I got a response along the lines of, ‘This isn’t Monica, this is Michael, but I have a fantastic ceviche recipe!’ We texted back and forth for a while as he explained his recipe step by step. A few hours later, I got to cooking and ended up calling this stranger to have him walk me through the process. He virtually cooked alongside me. Sometimes texting the wrong number ends up in an awesome ceviche recipe!”

Hilarious

“I loved this wrong number text I got a number of months ago. I guess the horror was that Edith never got that butter pecan ice cream.”

“I was at a friend’s wedding this summer and if we had song requests we were supposed to text the DJ with the request. So I took down the number (after a of couple drinks, I may add) and suggested ‘Every Step You Take’ by The Police. Long story short, a confused/angry man called me and had some words. I guess I messed up one digit and he wasn’t a Police fan!”

“I had a random number text me a year or two ago asking if we had a Spanish test tomorrow. Being that I wasn’t in school at the time, it was clearly the wrong number. But I responded anyway with the below. I’ve felt terrible ever since…let’s hope there wasn’t actually a test!”

“A guy who ghosted me sent me all the details to his family Christmas celebration via text about nine months after he stopped talking to me. Apparently, my full name is only a few letters off from his cousin’s. But I think I should have just showed up to give him a real fright!”

Do you have a good texting horror story to share? Text it to (206) 816-3677!

Madeleine Wilson

Madeleine Wilson

Content Marketing Manager at Zipwhip
Madeleine Wilson is the content marketing manager for Zipwhip. Her experience in brand strategy, strong writing skills, and eye for design help drive traffic to the Zipwhip website. She loves telling the stories of how Zipwhip impacts businesses and consumers.
Madeleine Wilson