Dating was hard enough before smartphones were invented—before the agonizing fear of accidentally liking a crush's Instagram photos from 2014 or the psychological torture of receiving read receipts. Being on our phones at all hours of the day has made texting mishaps the norm, not the exception. To help us cope with our own paralyzing dread of sending the wrong person the wrong message at the wrong time, we asked others about their worst texting fails. We vow to never repeat their mistakes… if we can.
I was texting this guy who had an Android phone, and I guess he wanted to mass text a bunch of girls. But the girls he texted who had iPhones were automatically put into a group chat. He had inadvertently sent out, "Hey, want to come over to Netflix and chill?" to over 11 of us.
I saw it and just laughed. For a while, no one said anything—radio silence. But as soon as one girl decided to call him out with a, "What the fuck is this?" the rest of us started, too. He never responded to the group.
I used to always think my boyfriend was cheating on me. Instead of talking to him about it, I did things to try to catch him. There's an iPhone feature that allows you to share your location with an iMessage contact. Once, when he was in the shower, I turned it on and went home to happily stalk his whereabouts during the day. He waited until the next time he saw me to tell me that he had received a notification about what I had done.
Instead of learning my lesson, I just brainstormed more ways to spy on him. I thought gaining access to his iCloud would solve all my problems. I already knew which email address he used for his username, and I knew him pretty well, so I figured I could guess his password. Whenever I was bored and on my computer, I would go at it. Sometimes I would try it while drunk with friends.
Apparently, he has incredible willpower—he never mentioned the dozens of "attempted log-in" email alerts until our final breakup fight.
My ex had a similar name to one of my mates. I wanted to break up with her, but we had been together for a long time, so I sought out my friends' advice. I proceeded to make a group chat and asked them their opinions. Many of my friends had issues with her, so they took the opportunity to be brutally honest.
The friend that hates her the most was weirdly quiet and never said anything. I thought it was odd and asked him, Alex, what he thought. Alexis, my ex, who I had added in on accident, responded into the group chat, "I get the point."
I was dating this girl and I had snooped in her phone previously. I thought she was cheating on me with a friend of ours, and one night I got drunk and started texting them both—telling them how terrible they were. It was 4 AM and the friend was awake, but my girlfriend wasn't responding. I assumed she was sound asleep.
My friend told me it was a huge misunderstanding and they had never hooked up, had never even thought of it. I freaked out and didn't want my girlfriend to think I was crazy (I had sent her some really vicious stuff), so I took an Uber to her house. I know she doesn't lock her screen door, so I thought I could stealthily walk in and delete the text message—no harm, no foul. Instead, I ran into her wide awake. She had already read my messages, too.
I was talking to two of my friends. The first person was annoying me so I was talking shit about her with my second friend. I kept taking screenshots and sending them, saying how dumb the first person was being. But I accidentally sent it to the person I was talking to. Luckily, I'm good at being shady. Once I had realized my mistake, I quickly took my phone and put it on airplane mode. I waited until it said, "Message failed to send." Crisis averted—until the week later when I did the exact same thing but didn't notice in time.
I'm pretty lazy and uncreative. I often Google search for sexting examples and copy and paste them into my messages. I guess I used something that was a little too specific once because the girl asked if I had gotten it off of the Internet.
*Names have been changed.