15 Mortifying Texts You Should Never Send Your Boss

What could be more completely embarrassing than sending a cringe-inducing text to your manager or boss that was clearly not meant for them? Once that regrettable text goes through, you simply can’t get it back, so until they reply, you are sitting on the edge of your seat in utter horror. And the feeling may be even worse if they never respond at all.

It's bad enough to do something silly at the office or make an honest mistake or have an innocent slip-up at work. But these things tend to happen, and for the most part, they are relatively easy to get past. Bosses do not expect their employees to be picture-perfect 100 per cent of the time, so a work-related blunder every now and then is par for the course. But there is a big difference between calling in late for a sales meeting and doing something far more unimaginable — like texting your boss something vile, rude, crude, inappropriate, or otherwise, just wrong. Is there an emoji for that?

These 15 examples of cringe-worthy texts that should have never been sent to a boss make us laugh, but the sender and the boss on the receiving end most likely had quite a different reaction. Some of these folks may have been let off the hook, while others were surely fire — perhaps via text. Texting is surely convenient, but not when it gets in the way of your career. Surely these people never made that mistake again!


15 No Love Lost

We are all for being polite or even complimentary to the boss, but saying, “I love you” is a bit much. And the added “baby” didn’t help matters. This texter must have felt like a fool by texting the wrong message to the wrong person. Surely the boss brushed it off as a silly mistake, but the sender surely had that moment of true humiliation. Let’s hope this boss kept the texting mishap to himself, or else this too-quick-texter will never live this moment down. At least he didn't say anything mean or nasty — that’s a plus in this awkward text exchange. Hopefully the fella composed himself and remembered to send his message of love to the right person after this moment of embarrassment. And maybe the boss did feel the love — if only for a moment.

14 Talk About Kissing Up To The Boss


We've all heard about kissing your boss’ a$$, but what about sending them a kiss via text? Who knows what this woman meant to send to her boss, but surely it was not a big smartphone smooch. Perhaps she texted the wrong person or just hit the wrong button. But either way, the damage is done and now the kiss is out there. Damn emojis! Hopefully her boss was understanding and let the kiss mishap slide, but some bosses can be stern and leave no room for error, even in the form of a kiss. This woman ought to remove her boss’ contact info from her phone so she doesn't accidentally send him another kiss ever again. Hopefully, the boss didn’t kiss and tell everyone else at the office!

13 Well, That Sucks

When you text your boss that she can "suck it" (among other nasty remarks), things are sure to go south from there. Obviously, this person sent their text to the wrong person, but now the boss knows how they really feel about her — and it isn’t anything close to good. And this boss has no sense of humor as we can see by her response. Putting down your boss is a good way to get fired, even if they weren't meant to know how you really feel. And to blame the mischievous mishap on your friend? Double damage. This quick-witted boss is a no-nonsense woman who won’t stand for foul language or lack of work ethic. Hopefully this person learned their lesson and never tried to play hooky again!

12 Life's Not Always A Beach


Let’s first hope that this person’s uncle is still alive and well. Nothing like lying about the state of health of a family member in order to have a week off to sun and surf at the beach. Too bad this beach-bound broad was dumb enough to text her boss the incriminating evidence. With the reply seen from the boss, this gal can spend far longer than a week at the beach — she’s now free indefinitely. If you're planning to miss lots of work for a made-up unforeseen circumstance, you had better have all your ducks in a row. Case in point? Do not text your lie to the one you are lying to. Seems simple, but for this person, her apology was too little, too late. Hopefully her days at the beach are filled with sunny weather and calm ocean waters.

11 Tied To Your Work

Well this boss must have had quite the eye-full when he received a naughty pic of one of his employees. Lingerie is one thing — and it is risqué enough — but add in the handcuffs and we’re at a whole new level of indecency. Sure, if this pic was sent to the woman’s significant other, that is their business, but send it to the boss and things are going to be troublesome. Who knows if the boss got a thrill out of seeing the sexy shot, but the woman must have been completely embarrassed. How could she go to the office again without wondering if her boss was picturing her in a bra and panties? This gal better zip up her coat and try to forget the whole thing even happened. The question is, did her mate ever get the pics intended for him?

10 If You Like Pina Coladas...


Don’t we all sit at the beach to heal when we're sick? Doctor’s orders! Take two aspirin, eat plenty of hot chicken soup, and sip frosty beverages beachside. Sounds like a medical miracle! Too bad this person blew their cover by revealing their sneaky plans to the boss. That piña colada must have been enjoyable while it lasted, but sobriety kicked in fast when the text about the day off was sent to the wrong person. Beach days suddenly turn ice cold when you are instantly fired from your job. The next time this person thinks about faking an illness, they had better remember to check who they are texting before they blow their cover. They are going to need something much stronger than a piña colada after this mess-up.

9 Let Him Sleep

There is no good reason to text your boss to see if they are up. Especially at 4:05 a.m. Who knows if this was a result of drunk texting or they really needed to know if the boss was awake, but the end result is a feeling of shameful regret. Unless this person works the night shift, a text in the wee hours of the morning is unacceptable. And the casual nature of the text makes it even worse. Who knows what the boss wrote back, but if they did, in fact reply, it must have been hours later. Not too many people are up before 6. If this person was drunk when they texted the boss, let’s hope this moment of embarrassment sobers them up. Don’t you wonder what they wanted from their boss at such an odd time anyway?


8 The To-Do Lust


Lustful isn't something you would point out on your resume, so it better not be part of a text exchange with the boss either. Of course, we see this is an unfortunate autocorrect fail, but it does not make the awkwardness any less embarrassing. At least the boss can see that their employee is a go-getter, it's just too bad they were too busy to check their spelling prior to pressing send. Hey, you can’t do it all! But what if this person did have such lust that it required many stops to satisfy it? Where would they visit to manage the lust? A lingerie store? An adult video hole-in-the-wall dive? These aren't the details a boss needs to hear. Thankfully, this texter realized their mishap in the nick of time.

7 Screenshot Snafu

Have you ever taken a screenshot of a text exchange to send to someone else so you can both pick it apart, ridicule the content, or use it as evidence for a future time? That’s all well and good if you send it to the right person, of course. But when you send that screenshot to the person you were texting in the first place, you are going to have some explaining to do. Particularly if it's a text convo with your boss. You can chalk it up to an accident, but they surely won’t buy that explanation. The awkwardness won’t go away, so you better have a good reason for having taken the screenshot to begin with. No more screenshots if you want to have a place to go to work in the morning.

6 Shocking Text


S*xting your boss is off-limits, but if it's done by accident, you may get a pass, and everyone can move on. But if you s*xt something to your boss but it was meant for your significant other, the boss may be shocked. You can apologize and hopefully they will drop it, but what if the boss is interested? And to make things even worse, they are married and still want to partake in the naughty text exchange. This is not going to end well. You may have been the one to make the initial error, but the boss is now the one crossing the line. End the convo immediately and fess up to your S.O. at once so there is no future confusion. Hopefully this person avoided their boss like the plague the next day at the office.

5 Don't Click Your...

When you call in sick, you better have all your bases covered. Which means you had best not send a d!ck pic to your boss. Seems obvious, but this texter was a real wiener and screwed everything up. Not only did this fella blow his cover for his made-up illness, but now his boss has a photo of his “manhood” on his phone. This is beyond embarrassing, and who knows if this guy still has his job. Hopefully the boss had a decent sense of humor or at least was willing to give this guy another chance. After all this mayhem, who knows if the guy ever had the chance to spend the day with his girlfriend. Goes to show you, calling in sick when you are not can only get you into trouble. What a...

4 Looks Like Victoria’s Secret Is Out Of The Bag


This gal must have felt like a total boob when she realized she had sent a risqué pic to her manager rather than her intended recipient — her boyfriend. Even if her manager forgave the slip up, this gal will forever know that he has seen her in nothing more than a little satin and lace. The embarrassment must have been over-the-top for this gal who removed her top. Let’s hope her boyfriend believes she sent the bra text to her manager accidentally, or else there will be a whole new issue for this chick to deal with. Additionally, you have to wonder if the manager saved the sexy pic or if he sent it to anyone else. From now on, it’s all turtlenecks for this woman.

3 Who's For A 7-Day Workweek?

Most of us work Monday through Friday, which would make getting a text from an employee on a Saturday or Sunday quite the surprise. But even more shocking would be a nude pic from said employee. When you accidentally send your boss a naughty and sexy pic meant for another person, you are going to feel the heat when you realize what you've done. The embarrassment you'll feel will be off-the-charts and the humiliation will be something that is hard to recover from. Not only will you be hiding your head in your cubicle come Monday at the office, but you will forever have to deal with the fact that your boss has a semi-nude photo of you saved on their phone. Maybe asking for a promotion this week is not the best idea.

2 Hard At Work


If you're not the best employee, then you had better be careful what you do on you off time. There is a chance you could make a silly and embarrassing mistake like this person did and text your boss some super racy, detailed information obviously meant for another person. Luckily, this boss seemed to be humorous and took the text lightly, adding in a little jab for the person’s lack of enthusiasm and dedication at the office. In the future, this careless person will be sure to put in some extra hours at work and to check who they're texting before pressing the send button. Maybe this awkward incident was just what this texter needed to become a more dedicated employee. But who was the text really meant for?

1 When You Love Your Job A Little Too Much

It's nice to have pleasant feelings about your boss, especially when so many people cannot stand theirs. But imagine his surprise when the boss got this sappy text from their employee. They may have been flattered, but it's obvious the text was not meant for them. Hopefully the boss laughed it off and did not share the goofy incident with anyone else at work. But even so, the text must have caused this fella a ton of embarrassment. The next day at the office must have been super-awkward and full of laughs between the two, unless the boss did not find any humor in the situation. Let’s hope this guy remembered to text his girlfriend after this blunder so the correct person was told how much they are cared for.


More in High Life