12 People On The Most Insane Thing Their Boss Has Asked Them To Do

Everyone who’s ever had a demanding boss knows how difficult it is to stand your ground and say no. The most difficult employer I ever encountered was at my first editorial job out of college. I would receive the nastiest, most brutal emails from him reviewing my work, only to have him leave his office and smile at me and ask me how my day was going. It was this jarring disconnect between how he communicated with me that made me terrified of ever turning down extra hours in the office, even if I had plans. On top of all of this, my editorial shift was from 2pm-10pm with an hour-long commute each way. The straw that broke the camel’s back, so to speak, was when he asked me to stay an extra two hours on my last night in the office before I moved back to Florida. I had already planned on having a going away party and staying at the office would have required me to miss half of my party. I told him no and was shafted from ever using him as a reference, which was a bummer since the amount of hours I logged there was astronomical.

However, I understand that my experience is singular and that other people have faced some insane requests from their employers before. Since today is Bosses Day, I thought it would be hilarious to ask 12 of my closest friends about the most insane and unreasonable things their bosses have asked them to do.

1. Unmentionables

“My boss once asked me to schedule him an appointment to get his “unmentionables” waxed then sent me a very strongly worded email advising me not to tell the rest of the staff. Yeah right, buddy.” – Caroline, 25. 

2. Big Box Of Condoms

“Once on Christmas Eve my boss sent me an urgent text to bring twelve bottles of red wine and a box of magnum condoms to her home in the Atlanta suburbs. I unfortunately had to oblige.” – Morgan, 24. 

3. Window Shopping

“Once my boss threw a book through her window out of rage at me, then asked me to call the glass people and order a replacement pane before work hours the next day. It was a rollercoaster.” – Jamie, 24. 

4. Too Large

“One time my boss asked me to bring a manicurist on set for her then when she saw the manicurist demanded another one because that one was “too large.”- Chris,. 29. 

5. Level Up for Promotion?

“One time my boss asked me to beat a level of Tomb Raider for his son because he couldn’t do it and was tired about hearing about it at home. He slipped me a $50 dollar bill but it all felt weird.” – Neil, 26. 

6. Nair Thank You

“One time my boss asked me if I would help him Nair his back before a ‘big date.’ Hands down the most harrowing afternoon of my life.”- Kyle, 29. 

7. What A Ham

“My boss would make me go and get him two lbs of sliced ham put into two seperate bags. If the deli forget to put each lb in a different bag my boss would overeat then scream at me because it was my fault.”- Jason, 29. 

8. Expensive Night Out

“My boss once had me write off an extremely expensive strip club visit off as a business expense because he brought an important client to one. I’m not sure who spends $5,000 on a strip club in a single night, but I had to file it under “entertainment.” – Barbara, 28. 

9. Trail Mixed Up

“My boss used to have me go through her trail mix bowl every morning and pick out every single raisin in there because she couldn’t stand the texture.” – Laurie, 24. 

10. Alibi Bye

“My boss used to have me call his wife and explain to her for various reasons why he wouldn’t be home for dinner. I later found out my boss was cheating on his wife and it was very upsetting to realize I had been helping him with his alibis for so long.” – Victoria, 29. 

11. Storytime

“My boss would have me take her two little dogs for walks around the park during business hours, then I would have to read them stories from books she had selected before they went down for their afternoon naps.” – Wendy, 26. 

12. Friday Flower Girl

“My boss used to have me order flowers for every single girl he was sleeping with at the time every Friday. Let me just say I was shocked at how many ladies he was pulling because I would order 13 dozen roses every Friday….” – Jocelyn, 31. 

Lead image via YouTube.

Share Tweet E-email