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24 Funny Bosses Who Sent Their Employees Some Hilarious Texts

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In the right circumstances, boss-employee relationships can be awesome. In fact, one of my fondest memories of my first job is running away into the forest screaming while my boss chased me with a 3-foot-long water cannon. Ah, the joys of working at a summer camp.

Recently, #TextsFromTheBoss and #TextsFromMyBoss have started trending on Instagram, allowing people to post about the funny, cute, wacky, and downright wild things their bosses text to them. We gathered up twenty-five of the funniest #TextsFromMyBoss, from peppy pep talks to nutty non-sequiturs, for your reading pleasure.

Just … maybe, if you want to maintain your relationship with your boss, wait to read these until you’re not at work, okay?

1. What’s the best part about this image: that the boss is sending it to their employee, that it’s not even a weekday, or that the boss has clearly decided to celebrate God’s day of rest by sharing work-related Jesus memes?

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2. From “I don’t care what you do” to “That’s a terrible idea” in less than a minute. In all fairness, if I got that kind of text message from anyone in my social circle, I’d probably respond the same way, especially if I knew I had to be working with them bright and early the next morning.

3. Admittedly, this isn’t where my mind would go if someone told me they had “a cold weenie in their car,” that they wanted me to see. But this little guy is way cuter, way more uplifting and, most importantly, way less likely to end in a contentious workplace harassment suit. Good choice there, Mystery Boss!

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4. I know, I know, this is the kind of adorable and uplifting message that makes you want to come into work happily even on the lousiest of days. It totally is. But can we also take a moment to recognize that his name is “Randy Jessup BOSS MAN”? There’s gotta be a story behind that. 

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5. This is literally the most ominous message I can imagine getting, from my boss or anyone else. “Take a machete,” from where, Mr or Ms. Ang Duck Island, and to what purpose? The people deserve to know!

6. It took the boss a full five minutes to realize he had sent the message to the wrong recipient, which is inexplicably hilarious, and must have been terribly confusing for the poor employee. (Also, the answer is Star Wars, natch!)

7. From the context in the initial Instagram post, it’s obvious that this employee works in nursing. Out of context, the phrase, “it’s kind of gross but it reminds me of your work,” would be hilariously mean. (Also, loving the employee’s enthusiasm for the bloody gauze!)

8. It’s time for another good game of “what’s the best thing about this exchange”: the fact that the boss got so excited learning about the creation of the humble chicken nugget that they had to send it to their employee, the fact that this exchange happened at eleven at night, or the fact that the boss’s only explanation for the baffling GIF is “chicken nuggets.”

9. “Back in my day, we ate all the foods that we were allergic to because we wanted to build up our immunity. While we were walking to school through four feet of snow, uphill both ways!” (also, “#diarrheaisforlosers” god bless).

10. During the Cold War, Mutually Assured Destruction was a military policy doctrine whereby both sides are discouraged from attacking each other because of the knowledge that the other side could completely obliterate them in turn. See also: the little nod of recognition you and your boss give each other when you both show up to work late and neither of you will ever speak of it again.

11. It’s nice that this boss has such a good relationship with their employees that they feel comfortable exchanging cute memes like this. On the other hand, I think if my boss sent me this wildly cursed and terrifying image, I would quit on the spot out of sheer dread alone.

12. Well, either way, this boss is looking out for their employees’ physical needs and emotional well-being, and I salute them!

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13. Wait, wait, you can’t just leave us hanging, mystery boss! What was the character arc behind John’s decision? What factors led to your knowledge of it? Was John ever freed?! You can’t just drop that text like it’s normal and reasonable and expect there not to be questioned!!

14. While these two texts are from separate accounts, I like to think there’s a story going on here. Like, the boss was really excited about their cool goth clothes, and their all night work ethic, and their shared disdain for silver jewelry and then they were like … wait a second…

15. While few bosses are solemnly-handing-you-their-high-pressure-water-gun-to-gently-encourage-reluctant-campers-to-get-out-of-bed cool, I’m willing to admit that there are some pretty cool bosses out there. 

16. This is the biggest adventure I’ve seen summarized in two minutes and five texts. Honestly, I can’t tell whether this mysterious boss had an awful last night, or a great one, or some combination of both. If I had to guess, I’d say probably both. 

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17. The caps transform this text from a mere amusing exchange into a work of art. The mysterious Yelp reviewer has not just called the employee an a**hat, they have called them an A** HAT, capitalization and breaks necessary!

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18.  Sometimes, your employers just know you. And sometimes, your employers know you so frighteningly well that you have to check to see if they’ve planted some kind of specialized NSA camera inside of your soul. This looks like a case of the second.

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19. Remember when I said, five minutes ago, that I had found the most frightening text ever sent by a boss? What a fool I was. What a sweet, naive fool. 

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20. Sometimes, two people in a conversation are working on entirely different planes, one much deeper than the other. And while the wise philosopher who quotes “Cotton-Eye Joe” is this case is not appreciated by their friend, one hopes their wisdom will enlighten them.

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21. Not only is this boss sending their employee reaction images, they’re clearly sending them reaction images based off of crafts they made at home. That’s adorable.

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22. Look, I know that employee loyalty is important. But I think there’s a gap between “I’ll stay after work to finish a project even though I don’t have to” loyalty and “I’ll take twenty-to-life for your sake” kind of loyalty. That’s just my opinion, though.

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23. This is proof that Twitter’s new 280 character-limit is b.s. because this exchange is three words long and funnier than any tweet I’ve ever seen. 

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24. The cutest thing about this text message: the fact that it’s completely unprompted by anything, or the fact that the boss sent it first thing in the morning, clearly so delighted by their employee that they couldn’t wait a moment longer to tell them?

24Emily Pollock

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