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Amusingly Horrible Things Bosses Have Said: The Bracket

Bosses sometimes say amazing things, so we asked you to anonymously pass along the best you’ve heard, and we made it into a tournament. An impartial judge picked the “winners.”

1. [After I pledge to fix a minor office problem:] “Stop being all CALM. You’re doing that thing again where you get all CALM on me. Do you understand why I’m upset? I want you to be upset too.”

2. “Your handwriting is awful. You really need to take some time to find yourself.”

3. [I sprained my ankle, but didn’t have crutches. It was summer. Boss turned off A/C in our office, so I explained that even walking around gets me sweaty now (due to sprain/limping). His response, having forgotten that I had sprained my ankle:] “Jesus Christ! I know people get out of shape in college, but really?! You need to get back to the gym!”

4. [When I told her I was pregnant:] “Did you do that on purpose?”

5. [During my six-month review:] “Your goal for the next six months should be to find a new job. I don’t think you have what it takes to make it in fundraising.”

6. “Is [new employee] the one with the [mimes cupping large breasts, raises eyebrows suggestively] or the fat one?”

7. “It’s good for you because now you can spend time with your boyfriend.”  [As I’m being laid off from a global PR firm where I held a senior level position.]

8. [Right after confessing that I was in the process of confronting my alcoholism, getting sober and might need to adjust my work schedule:] “…so you’re going to be a slacker now?”

9. [I had to go in for a biopsy to find out the status of potentially cancerous cells. The procedure ran a little later than usual so I emailed my boss to let him know I’d be 30 minutes late coming in.]
Boss: “So, what did you have to go in for today?”
Me: “It was a biopsy.”
Boss: “Oh, neat. Can I see where they did it?”
Me: “Um, no.”
Boss: “Oh, really? Maaaybe it was because you didn’t actually go to the doctor this morning? Hmmm?”
Me: “It was from the cervical area.”
Boss: “So, can I see it?”

10. “Next time, remind me not to hire anyone with kids.”

11. [When our very small company moved to a new office suite, none of us employees were involved with the actual moving; the boss hired movers to move everything. When I arrived at the new place on Monday morning, the boss led me to my new quarters. It was at the end of a long corridor.] “Oh,” I said, pleased, “I get my own private office now!” As he turned to leave he replied, very sincerely, “Yeah, I learned a long time ago that in business you put the prettiest girls up near the front, where customers come in, and the plain ones in back.”

12. [At a happy hour on my first day as an intern, my new ‘tipsy’ boss kept introducing me by saying:] “This our Monica Lewinsky.”

13. [After explaining to my boss that my boyfriend’s younger brother was hospitalized the night before from an overdose of heroin and Klonopin:] “Oh. Good! When you said he was ill, I assumed it was something terminal like cancer!”

14. [After making me re-interview for my job and then firing me:] “It would just be unfair if I let you hog the position. You don’t mind training your replacement, right? It’s the least you could do.”

15. Boss: So you have a tattoo?
Me: Yes, it’s of Nebraska [where I’m from].
Boss: So you’re one of those girls.

16. “I mean, it’s not like you need a degree to do this.” [I have a degree.]

17. [Explaining why he was firing me the day after I returned from a “vacation” visiting my grandmother on her deathbed:] “Too many people get sick or die in your family.”

18. [While trying to come up with a job title for my role designing fliers:] “I’m not going to call you a graphic designer… that would be an insult to graphic designers.”

19. “Will you please talk to my attorney in this sexual harassment case,” [which was actually filed by a jilted but very smart ex-girlfriend], “since, you know, I actually sexually harassed you and you still have a job here?”

20. [First thing out of my boss’s mouth upon my entry into the office:] “You look haggard this morning!”

21. [Every year, my boss would have us decorate the department for Christmas, including stockings, a Christmas tree, and, no joke, a manger. And every year she would invite the entire department into her office to listen to her rail against the company memo that invariably circulated urging department managers to hold “Holiday” parties and keep any seasonal festivities secular and inclusive.] “If you don’t believe in Jesus Christ, then you have nothing to celebrate,” she’d say. Then later she’d call me into the office and say she hoped she hadn’t offended me because my husband is Muslim.

22. “I’m sorry about your diagnosis [of a degenerative disease], but I have always found that the cure for any disease is just to have more sex.”

23. [After learning that a second trimester miscarriage was the cause of my tardiness:] “Well it’s a good thing that happened now! Man, I bet you’re sure relieved.”

24. [Upon seeing a photograph of me:] “Wow! What a great picture! You know how some people look so good in person but come out looking just awful in pictures? With you, it’s just the opposite.”

25. [At my last fashion retail job:] “I’ve found that attractive salespeople get too distracted by flirtatious customers. That’s why I never hire them.”

26. [A few Fridays in a row my boss asked me if I had weekend plans. Unfortunately, for these few weekends, I did not. One such Friday afternoon, in an unrelated bit of conversation, I briefly mentioned that my boyfriend and I are involved in a long-distance relationship, and she said:] “Oh, so that’s why you have no life.”

27. “I don’t believe in taking antidepressants.”

28. [While I tried to gently and discreetly discuss with my male boss the untidiness of our shared bathroom (i.e. floor pee), he says:] “So you think that I did that? Did you know that I have to kneel down to pee? Because of a piercing that I used to have in my penis. I do. I have to kneel down. To pee.”

29. [Working as a copyeditor at a vanity publishing company, I had written that a manuscript “prob. needs major cuts.” Boss called me into his office and read me my note.] “P-R-O-B? What the hell is that supposed to mean?”

30. “I called this meeting because I think we need to talk about the level of professionalism at this office [spits tobacco into a clear plastic cup].” (THIS LITERALLY HAPPENED)

31. [On the phone with his girlfriend in a baby voice:] “Oh nice, baby, nice! That’s really cool, babe. Baby, you should make that your Facebook status update! I said you should make it your Facebook status update. Your Facebook status update. I said you should make that your Facebook status update. On Facebook. You should say that on Facebook.”

32. [After multiple people had complained about the office being too cold, a boss walked by me wearing a scarf and gloves at my desk:] “Looks like you need more blood.”

Previously: Things Moms Have Said, Things Significant Others Have Said.

Next: Amusingly Horrible Things Strangers Have Said. Please submit!

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