30 Extremely Awkward Interactions Between Employees And Their Bosses

Imagine having to see them at work the next day

Kylin

• Published in Funny
• July 5, 2022

When we are all living in the world of technology and social media, it is inevitable that you’ve sent a message to the wrong person, or talked about someone in a group chat, forgetting they’re in the same dang chat. It’s just part of life as we know it now.

Then there’s the extra painful experience of sending a text about a person TO THAT PERSON. Or even taking a screenshot of a convo about a person and sending it to them on accident.

Say it with me now: "Ooof." If you can imagine, those cringey and embarrassing exchanges are actually capable of getting much worse.

We were able to collect texts people sent to their bosses on accident, and HOO-BOY, it’s rough. But, it’s also hilarious, and we’re so grateful for the existence of the internet that has allowed people from all over the world to share the most awkward interactions, in person or over text message, that they’ve had with their bosses.

From people having bosses that share the same name as their besties or spouses, to accidental selfies and a sprinkle of autocorrect mishaps. We have something for everyone with these 30 tweets about awkward or otherwise embarrassing exchanges with bosses.

Keep scrolling to see more!

1. This text was meant for his girlfriend. Oops!

2. Dallas wasn't taking it anymore

3. Do not nap and text under any circumstances

4. They're going to learn quickly that they gotta start locking their phone

5. Imagine professing your love for your boss. Ultimate cringe? Yes.

6. Accidentally oversharing is a curse that none of us should have to endure.

7. Pretty sure that's sexual harassment

8. That's cold, but they have got a point that you can't really argue with.

9. When you forget to use your work-friendly vocab

10. Pepper spray is not in the budget!!

11. "Tomorrow we can touch."

12. Sounds like she made it the manager's problem and that she is a total boss.

13. No, I don't think I will... thanks tho

14. They were not joking

15. Sweet, sweet, vengeance

16. Accidental, but very cute, flirting. You kind of love to see it.

17. Naïve, but not like it was a huge stretch to assume

18. Saying is very different than asking

19. There's never a wrong person to send a cat picture to

20. That was a wild ride

21. Potato boss

22. Oops

23. Get it together, Matt

24. That sinking feeling of impending doom

25. Could actually have been worse based on their response

26. Oh, no

27. Copy that

28. Double check your group chat members

29. Even more awkward

30. Too many Shannons

I am so glad the internet exists for stuff like this. There’s some cathartic about another person’s incredibly awkward or embarrassing interactions with other people.

Have you ever had an awkward text exchange with one of your bosses? We want to hear all about it, so please drop your stories in the comments section below!

Don’t forget to share this with another awkward friend!

Kylin