Embarrassing Tech Mishaps: The Naked Skyping Edition

iPhone Life readers share their most cringe-worthy tech mishaps—from naked Skyping to parental sexting. Have your own mortifying mishap to share? Email us at techmishaps@iphonelife.com. You could be featured in our next column!

Related: How to Change Auto Lock Time on iPhone & iPad (& Fix It When Greyed-Out)

Naked Skyping 

“I was on a conference call while working remotely, and apparently halfway through a presentation, my husband wandered across the screen behind me in his birthday suit. I had no idea at the time. It wasn’t until my boss broke the news to me a couple months later over drinks that I became aware of what had occurred. My husband is lucky he didn’t get me fired!”

- Not-So-Professional After All

Awkward Dad Moment

Personally, I haven't made a mistake since before I had a cell phone. ;) However, I did receive a text from my dad early one morning that read, "I had a really nice time sleeping next to you last night." I responded by saying, "I don't know about you, but I slept next to my dog last night."

- The Snarky Son

A Serious Chick

My wife was emailing back and forth with a guy in her company’s New York office. She informed him of a policy that he found pretty irksome, so he forwarded her email with the headline, "Is this chick serious?"... Except, he hit reply. She answered back and copied the director of HR: "Yes. I'm quite serious. Thanks." There was a lot of explaining that dude had to do.

-Don’t Mess with My Wife 

My Mom Said What?

Tinder should come with a breathalyzer test! I had a few glasses of wine over dinner with friends and I was lying in bed texting with my college-age daughter while I swiped through profiles on the dating app. I matched with a cute guy, who had apparently had a few drinks himself, and we started messaging. Things quickly got flirty, with racy jokes and innuendo flying back and forth. In the course of this banter I made a joke about him sending me a risqué pic. Only problem was, I accidentally texted it to my daughter instead of the guy. She’s never going to let me live that one down!

-Worst Mom Ever

Apple Watch Fail

I was in bed with my girlfriend the other night, and things were getting pretty steamy. My wrist must have been at a weird angle because I somehow triggered my Apple Watch’s new SOS feature (which calls emergency medical responders when you press and hold the side button). Suddenly we heard a siren sound filling the room. The lesson? Don’t wear your Apple Watch in the bedroom.

- The Boy Who Cried Wolf

Accidental Home-Wrecker 

Once, I texted my husband, “Are you asleep? Are you naked?” I did not realize I had transposed a wrong number in his contact card!! I received a text back from someone saying, “Who the F*%k is this?” I replied, “I am so sorry, I meant this text for my husband!” To which I received another text: “Don’t lie to me, I know you are that little tramp who is fooling around with my man!!” I immediately blocked the number, but felt awful, knowing I caused a problem for an innocent (or maybe not-so-innocent) person. Needless to say, I have never sent a text like that again!!!

- The Other Woman

How to Get Fired

“A freelancer kept showing up late for work, so I texted to remind him to come in. He must have mixed me up with one of his friends, because shortly after I got a response letting me know that work was ‘killing his vibe’ and that I’d ruined his plan to enjoy some recreational drugs with his buddies instead of coming in to the office. Needless to say, he doesn’t work for us anymore.”

-Vibe Killer


I don't usually delete old messages on my phone. Especially old group texts—they can come in handy sometimes. But you know when they’re not useful? When you're crossing a busy street in Brooklyn excited to text your boyfriend a scandalous version of a new dress (in various stages of the outfit). Because sometimes, you accidentally send the message to the group labeled, "boyfriend and boyfriend’s mother." 

-Kill Me Now 

Voice Memo Woes

My cousin has one of the thickest southern accents I have ever heard in my life. I found it super amusing, so I used my phone to secretly record a conversation of ours so that I could show it to my friends later, but when I tried to save the recording, I accidently played it instead and couldn’t turn it off! My cousin just went silent and stared at me. I was so embarrassed that I just walked away without any explanation.

-Not-So-Sneaky Cousin

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iPhone Life Team