Creepy Boss stories: our readers share true tales of their grossest, weirdest employers.

Creepy Boss stories: our readers share true tales of their grossest, weirdest employers.

Last week, we reached out to readers for stories about creepy bosses, and responses flooded in on Facebook and email. Thank you so much for sharing all these hilarious (disturbing, lawsuit-worthy) details. "Creepy" is a big word, including the openly lewd, the possibly dangerous, and the mostly pathetic. From the guy who manipulated a woman's new apartment to managers who managed to get their crotches on employees' shoulders every day, it's amazing the diversity in terribleness. We got so many that we may do a follow-up, but here are 18 of the best submissions from our readers:

1. There's nothing creepier than Halloween, right? Wrong. As Patty told us on Facebook, working in a temporary Halloween store in high school can be way worse.

In high school I worked at a store that sells party paraphernalia. During Halloween the creepy middle aged male boss made us wear costumes, but he got to choose them. It was never anything appropriate; for instance, I was a Dallas Cowboys Cheerleader. At the end of the night he would choose one of the girls to clean the restroom, but he would "supervise" the whole time to make sure we cleaned it right. I can remember being on hands and knees scrubbing a toilet in that skimpy outfit with his shadow cast over me, so close I could hear him breathing... :( I quit before the end of the Halloween season.


2. Here is a submission from a reader who wished to remain anonymous. Her tale of a training seminar for bad decision-making is a reminder that one person's creepy boss is another's really stupid romance.

As a newly hired store manager for a national cellular phone company, I had to attend a week-long training seminar in different town. I shared the 6 hour ride with another newly hired manager from the district. This could have been awkward, but to my relief, we had enough in common - we were both married females in our early 30s with young kids - to make for a pleasant ride.

After our first day of training, our District Manager (I'll call him "Dick") invited the training class out to dinner, and my companion (I'll call her "Jane"), immediately started binge drinking and had barely eaten any food. After her 5th drink, Jane ran into the bathroom and stayed there for about 20 minutes; as the only other female in the group (and her ride back to the hotel), I had to go check on her.

Jane was sitting on a toilet in an open stall with vomit in her hair and all over her clothes; she stunk! I convinced her to let me to help her clean up before we went back to the table to say goodbye and head to the hotel.

She agreed that she needed to leave, but as soon as we got back to the table, Dick announced that he had just gotten another round for everyone, to which Jane screamed "WOOHOO!", sat down next to him, and began to flirt.

I stepped outside to call my spouse and vent my disbelief. When I got back inside, I headed into the ladies room, and there I discovered Dick and Jane making out! Keep in mind she smelled strongly of vomit. Very strongly.

I insisted that we leave immediately, but she started crying, and Dick said that he'd give her a ride back to the hotel later. No way - I refused, and had legitimate concerns for her safety.

About 10 minutes after we get back to the hotel (surely Jane had passed out by now, right?) she knocked on my door and said that Dick was on his way to pick us up and go out to another bar! At this point, what could I say? She's an adult! I declined the invitation, and recommended that she just try and get some sleep. She said I was probably right. Probably!

The next morning, she was late meeting me in the lobby, so I headed towards her room, and who did I see walking down the hallway? You guessed it - Dick! Since he - and his wife and kids - lived locally, he was NOT staying at the hotel. The rest of the week, they got trashed every night and screwed, while I ate take-out in my room.

About two months later, Dick moved to a town within our district, about halfway between my store and Jane's. Shortly after he moved, he called me one day (at the store!) to ask if there was anywhere local that his "wife" could get an abortion.


3. This next story comes from Yasmin, who wrote us to tell of a slow-build of creepiness she experienced while working abroad that led to her escaping on the next flight out.

I started a new job a few years back. After about 10 months, the main boss left the country and left his friend in charge.

I was 25 years old. I loved my job.

One day, I got a call into the stand in bosses office. I entered, he asked me to sit down, he started discussing work, and then moved on [to talk] about his personal life. A bit too much for someone I hadn't met before, but I shrugged it off.

It happened the same time the next day, the day after and so on. Each time getting more personal about his wife and he separating.

I started hiding between classes I was teaching so no one could pass the message for me to go to his office. It worked the first two days, the next day was my day off. I got up and dressed and headed to look around the local shops. When I got back, my stand-in boss was outside my home talking to my landlord! It was strange, but I figured they must know each other.

As I was approaching my home, the boss said, "I've given in your notice for your home, the big boss said we should upgrade you for all the hard work you have done."

I didn't think much of it as part of my contract was free accommodation.

The move was 2 weeks away. I kept asking to see the new home, but he said I couldn't until the day before moving. I just took his word.

Strange things were happening at work. My things would go missing and HE would find them and drop them off to me, I was grateful the first time but then it became creepy.

I would get phone calls late at night asking "work" questions, always leading on to how good we were "together."

I started ignoring the calls out of work, [and] he would question me the next day.

One evening, I was working late. I was the only one there (the janitor lived upstairs), [and] I was about to get my things to leave and HE came walking in. I didn't hear the door go or anything. It really scared me. He offered to walk me home, which I politely declined, so he walked behind me the whole way home.

Next morning, [it] was time to visit the new home. When I arrived, it was a derelict building with just 2 flats inside. The empty flat was beautiful, [but] as I was walking around, I opened a door it led into another flat. Looking confused, I asked [if it] was part of my flat, and he said it was his flat! He had taken the lock off the door so we could "go in and out of each other's" whenever we wanted too!

This job was abroad. I left the country on the next flight I could!


4. On a lighter note, Chalky brings us a boss who is completely harmless, and only really "creepy" if you're Keith Urban.

The married, male owner of a place I worked at for years had this overly obsessive thing for Keith Urban. He once described him to me as "having the voice of an angel", and being the greatest guitarist alive. During the months that Urban was on tour in the southern US region, he and his wife would attend at least 1 show a week, at times going on mini-tours of 3-6 shows at a time. He always marked a "KU" on the calendar for all the days he'd be traveling to shows. He would literally stop you in the middle of a lunch shift, at a very busy deli, to show us YouTube videos of Keith. Our store security pass code was "Keith Urban" for christ sake! HA! Really creeped me out.


5. Our reader Jim recounts a story from his butcher's shop that demonstrates the principle that it's when people think they can get away with stuff that they show their true colors.

I'm a butcher and I had a boss who once did this.

It's closing time, as we're walking out the door, a lady who could not speak English very well came in and in broken English said, "I need chicken! I need chicken!"

My boss reluctantly went into the cooler and brought out a chicken for her. She then proceeded to inspect the chicken by turning it around and smelling the inside of the cavity.

We were all stunned when my boss, (just like in the movies) actually said, and I quote, "could you pass that test?"

Fortunately, her English was not very good and I don't think she understood what he said, but that incident has stayed with me for a very long time.


6. Jessica's old boss manages the impressive feat of sexually harassing people from within a single-occupancy bathroom.

When I first started working at my old job, my boss would use the washroom (unisex) and leave the door open every single time! It was a furniture store, and the washroom was in the back where it was all storage and boxes and stuff. One day I turned the corner to get to the washroom, and saw him standing there, door wide open once again, pants down and taking a picture of his penis. I guess I should have complained to someone higher up, but I just walked out the front door that day and never looked back.


7. Another Jess from across the pond wrote in with a story of a boss who went the very classical creepy route. It's practically old-fashioned.

I had a very creepy boss and his girlfriend wasn't much better!

The summer of '92 I got a very short-lived job as a waitress in a cafe at a popular English tourist destination . There was a cabinet at the front of the cafe with cakes and strawberries displayed in it. My boss would stack his porn mags behind it, out of sight of the unsuspecting customers but so we waitresses had to lean over them to take an order. There must have been hundreds of them. Sometimes he'd open up the magazines and leave the pages displaying his favourite pictures. He also used to call the sex lines that were listed in the back of the magazines- he kept a list of rates for each service on a pad by the phone: £20 for a blow job, £10 for a hand job...

His girlfriend would come and hang out in the cafe and one of the most traumatising things that would happen would be turning around and catching her with her hands down the front of his pants.

I think the cafe closed after just 6 weeks of being open - failed on the hygiene inspection.


8. Here's another "classic" creepy boss from an anonymous reader, except where the other dude was a "classic all-around creep" boss, this guy is a "classic trying-to-have-sex-with-you" boss. Passive vs active, basically.

My story goes back about 15 years now, when I was a younger, hot 20 year old.

One of my first office jobs was at a law firm in NYC and my mom knew the lead partner at the firm, who helped me out with a job. Another one of the partners (who was probably 20 years my senior at the time) took a liking to me (he was a bit of a ladies man). He lived out in the City (I lived on Long Island at the time)in a fancy apartment, and had invited me over for dinner, right around Christmastime. I (being the naïve 20 year old I was) took him up on his offer.

When I arrived, he had a romantic dinner with 2 gifts for me.

We started eating and he started asking me all kinds of sexual questions, like if I masturbated and how many men I had been with. It was all sort of uncomfortable, but I made it through and said that it was getting late and had to catch the train home. Before I left, he insisted I open the gifts.

The gifts turned out to be a vibrator and a giant pink dildo.

I promptly quit that job, and never spoke of it again.


9. Here is a very short story from Lori that nevertheless tells you far more than you'd like to know.

When "Step into my cubicle" turns into "Check out this new tattoo on my ASS"... TRUE STORY #creepybossstory

10. Where exactly these stories took place is unclear, but two women going by Blue Nymph and Cindy shared the most interestingly creepy boss on this list. (On further review, it may also be Lori's butt-tattoo boss.)

My x-boss (woman) would call my co-workers and I (we are all female) into her office to look at porn. Specifically so she could show us who John Holmes is. This same boss also dropped her pants for me on my first day to show me her "cafe au lait" marks (birthmarks) on her inner thighs. I have more upon request.


Obviously, more was requested.

One day, she came into the office and decided she didn't want to wear clothes. She goes to her office, strips down to bra and panties and shuts her door. About an hour later she has to go to the bathroom. Her office is at the back so to get to the bathroom she has to come up the hallway, past my office, past co-workers', through the door separating all of our offices and into the lobby (completely open to anyone walking in), down that short hallway and into the bathroom. Rinse and repeat to get back to her office.


And more

Once when she was "sick" she spent the day crawling around the office.

Her former coworker Cindy chimed in with backup details.

...until a client came in that she liked and then she jumped up smiling and perfectly fine.

But she wasn't just insensitive to people who don't like nudity or crawling, Blue says.

that's right. Or unless a (terminal?) cancer patient came in and she (boss) had to point out THE skin cancer DOT on her (boss') face that a CREAM got rid of .........


Surely, that must be it, right? Oh no, Cindy has more.

and the time she went to her sisters wedding and made sure SHE (boss) had the first dance and then tore her meniscus and made a scene and couldn't figure out why her sister was mad at her.

Ok, well, there's no way to top that.

oh my god. I forgot about that....having to get into bed with her to review files.

Ok, you guys win.


11. Let's get back to something we can all understand, like Ramiro's relatable story about textbook (and frankly cliché) harassment.

I'm a pizza delivery dude, and when I got transferred to another store, there was this girl that was training to be a manager who was clocking me out before we closed one night, and I was complaining about my lack of tips that night and she puts her hand on my leg, looks me in the eye, and says in what I think she thought was a sultry voice (but I just found creepy), "It's alright, I'll give you a tip later."

I nope'd out of that as fast as possible.


12. Adam shared a tale as old as time: a company covering its tail after a blatant crime and then firing the person who complained and cooperated.

TL;DR version: my wife was groped by a fellow supervisor in front of me and 100 employees. Company handled it shadily, we didn't sue, company waited a while and fired me, but ultimately there's some comeuppance.

I was one of several middle-management supervisors at a medium-sized call center, where my wife was an employee. All employees could go to any manager for help, but they all had assigned managers who went over their stats, etc. My wife, for obvious reasons, had a different manager than me.

During a night shift where only he and I worked, she would always go to him for help so as to not make it look like I was involved in favoritism/nepotism. One time when she went to him for help with an angry customer he straight up groped her inner thigh, mere millimeters away from her lady bits. He did this in front of me, and nearly 100 other employees.

It was taken up with the entire boss of the call center, who had a penchant for being coked out or high while at work, and he wrote it off like nothing happened. Persistent insistence by me got them to handle it by first not allowing him to interact with her, then suspension, then firing. It took a long time and a lot of terse conversations between me, HR, and the main cokehead boss before it happened. In the end, they never even acknowledged it to my wife and never directly apologized to her over it, instead giving me a halfhearted apology to pass on to her from the management.

During this whole thing, the head of HR was so angry she showed me how this manager had had five previous incidents of sexual harassment against the female staff, and how she had personally been uncomfortable around him.

A couple weeks later, we had a managerial meeting where a sexual harassment lawyer gave a presentation on handling stuff like this, where a fellow supervisor (who was just slightly above me and thus kinda a boss of mine) blurted out everything that happened to my wife, and how the company handled it, and the nice lawyer told us the company royally screwed the pooch, and then not-so-subtly implied I could totally sue their faces off.

My wife and I met with a lawyer, and she told us to expect backlash even though the law specifically states a company can't retaliate against someone suing them who still works there, pretty much every employer still does which then leads to another lawsuit, which can be lengthy and I'll still be unemployed. Since I was climbing their corporate ladder and was making the best pay of my young life, we decided not to sue and that was the dumbest decision ever.

Fast forward to the EXACT DAY after the statute of limitations to sue over this incident had passed, and I was called into the main boss's office, where I expected my long, year-and-a-half-overdue raise (as per the employment contract) would be given to me, but instead I was let go for the following reasons: "Being twenty minutes late during a blizzard. Switching a Wednesday and Thursday shift with a fellow supervisor (because she had an emergency) without getting pre-approval (as she called me on that wednesday), and being sick one time with an emergency room doctor's note, in an 18 month period." with the caveat of "We expect better of our supervisors."

At the time I was mid-move, and needed money and they offered me two months severance pay if I signed a contract saying I would not sue for wrongful termination. Ah to be broke, naive and 25 again. I signed it, got my monies and left.

The story has a somewhat satisfying ending. No one would hire creepy manager after this, and he wound up moving out of state. I eventually got a really sweet, waaaay higher paying graphic design job in the same damn complex as that call center, and I literally parked in the same parking lot. One day, and this was 2 years after I was fired, the main cokehead manager saw me walking to my car and asked me what I was doing there, and I said, without missing a beat (possibly one of my proudest moments ever) "I've waited 2 years and come back for my revenge." He nearly shit a brick, then I said "dude I'm just effing with you. I work next door at a much better, high paying job. have a good one," to which he sorta awkward laughed, and I never saw him ever again. The call center lost its best corporate contract and closed. Everyone came to work one day and was let go.


13. Sometimes, it's the little things that are the creepiest, as Stefany's "ghoul" boss makes clear.

Many years ago I had a boss who would grab and/or scratch himself indiscriminately in the office. But the creepiest thing by far was feeling the heat from his crotch against my shoulder as he invaded my personal space. He did that to all the girls. Still makes me shudder ... dirty little ghoul.

14. Here's a totally non-sexual creep, which may actually be way scarier (although people do serve their time and have to live their lives).

I worked in a Catholic hospital and there was a rumor that my boss was a murderer and has spent 20 years in prison. Come to find out it was true and we worked in the laundry room which is a glorified basement... with a murderer. Weird experience...I was confused about why he was a manager, at a hospital! Nobody warned me (by the way your boss is a convicted murderer) that would have been nice.


15. For whatever reasons, Brittani's small story is one of the grossest.

I think the one that shoved his hand DOWN my shirt to touch my stomach when I was eight months pregnant was my personal creepiest, though several have tried to take the title.

16. Some bosses are creeps every day. Others, like Amber's, just need to have a slightly extra-long lunch.

Married owner of a company I worked for took all of us in the office for a thank you lunch. After a very expensive lunch with much free flowing adult beverages, we all walked through the casino mall where we passed a Victoria's Secret. Stopping in front of it, he then proceeded to grab my arm and say "I think it's time to institute a new uniform for the office" and told the group I could model it. Creep factor times a thousand!


17. One reader, Kevin, wrote in to remind everyone that being an attractive man can also be unpleasant at work.

My creepy boss story has gotten quite a few laughs from anyone that's ever heard's an interesting one.

I'm a guy and when I was 18-21 I had a female manager that was around 50 years old. Working in retail, I worked directly alongside her many days. After awhile, she began making a lot of comments on how well I dressed, constantly asked if I worked out, and complimented how strong and fit I was. Now, with a 30 year age difference and the fact that I was in a relationship (as was she), I had no interest in her at all so it just made for a strangely uncomfortable work environment for 3 years.

Eventually, she started asking me to come over to hang out when I was off and I always politely declined. She even went as far as to ask me to bring my dog to play with her dog (as we both had pugs) which seemed innocent enough, but obviously I didn't care to do it and politely declined. Finally, one day at work she asked if my girlfriend was working late (she was) and mentioned that her boyfriend was working late too so I should bring my dog over so they could play and her and I could "relax in her hot tub". That was the last straw and finally I had to report her to HR...ultimately, she resigned as manager and moved to a new company.

It was an ongoing joke around the store the entire time I worked there (very awkward) and to this day if I see her somewhere, I immediately go the other way. Typically, most sexual harassment stories are the other way I like to throw my story out there so people know it DOES actually happen to guys too!


18. Finally, here's a feel good story from Roxanne about a bad feel and a quick revenge.

Here is a nasty one. Before being a nurse, I was a single mom and worked two jobs. At my one job my boss and I were counting the till at the end of the night in his office. Where he then closes the door and says that a gf of mine told him I breastfeed my baby, then he asked if he could see my boobs and gobble up the juice. No lie, he freaking said that. I knocked him off his chair and quit.

I knocked him on his Ass.