June 26, 2020 | Maria Cruz

People Share The Stupidest Questions They Were Asked At Their Job

When we’re on the job, we get asked a lot of questions during our shift. Plenty of them are the typical kinds we fluff off, but there are some serious head-scratchers out there. These questions were borderline responsible for workers losing all faith in humanity.

#1 Willy Wonka Machine

I worked at Kinkos and was in charge of a few different things for customers. On three separate occasions, different people angrily asked me why I returned their faxed document to them. They thought that a fax machine was some kind of Willy Wonka thing that sent their original piece of paper to the recipient.


#2 Why Wouldn’t They?

My ex-wife thought our cat’s nipples were something to be concerned about. She thought he had something on his stomach because of the bumps. I went to check and I was like, “That’s one of his nipples. See? There’s another here and here and here.” She said, “Wait… boy cats have nipples?” I happened to be shirtless at the time, looked down at my chest and said, “I don’t see why they wouldn’t.”


#3 Buying for Keeps

At a bookstore I worked at, we changed our return policy from one month to 14 days. Honest to God, there were so many customers who angrily shouted that they can't possibly finish a book that fast. We calmly told them that that was the point. We aren't the library. When you buy a book, it's so you can keep it.


#4 Fax It to Me

I used to work in a call centre for a large bank. A customer phoned while he was in one of the branches and said the queue was too big, so he wanted me to help him. I asked what his query was and he said the ATM was broken and he had to withdraw cash. I asked how I could possibly help him withdraw cash from the bank over the phone and he said, "Why can't you just fax it to me?"


#5 Take Care of This

I was renovating a major hospital when the owner changed their mind (again) and wanted to change the plan after we started construction.  "You guys can take care of that right, with no extra cost? Oh, and the end date won't change, will it?" We sure can't Steve, and it sure will! Those changes are going to cost another $100,000! And now we need to go buy completely different materials and figure out what you’re talking about. The schedule is messed up now. This is why construction never ends on the first given end date.


#6 Billy Bob Persona

This happened a few years ago when I was towing this one guy’s car to a dealership. At one point, he turned to me and asked, "So what do you do for a living?" He was completely serious. He automatically assumed that I had another job because I didn't fit the Billy Bob persona he associated with tow truck drivers.


#7 Wireless Laptop

I once got a call that a user's laptop was on the fritz and wouldn't power on. So, I went to check it out. I pressed the button, no life. Plugged it into the power and it started charging. Then, I pressed the button and it booted just fine. The user wasn't plugging the laptop into power because she "thought we had wireless.”


#8 Eight-Piece Chicken

I used to work at a grocery store deli. My co-worker, for some reason, got more stupid questions than anyone else. But one went a little like this: "Hi, what can I get you?" "The eight-piece chicken... how many pieces are in it?" "How… How many pieces are in the eight-piece chicken? Um. There are eight pieces in the eight-piece chicken..." "Okay, I'll have that, please!"

To be entirely fair, the lady was really nice about it, but "How many pieces are in the eight-piece chicken" is still a stupid question. A few people said, "Maybe she meant how many of each piece." No, she meant how many pieces are in the eight-piece chicken. I said eight, packaged it up, and she went away happy.


#9 Sign Your Name

I was volunteering as a cashier at a used book store for the library. In came this older fella who bought a big stack of books for 10 bucks. He was really nice and chatty, though he didn’t seem completely aware mentally. Not a big deal, I just had to explain sales tax and the book pricing a couple of times before he seemed to get it.

He paid by credit card and I explained how to sign the touchscreen for the payment to go through. This was where he asked for my name. I told him. He then took the iPad and said he really appreciated my service. Then, he happily told me he was going to sign my name for the card so “they” will know to send the money to me.

Before I could say, “No wait,” he submitted the signature. I couldn’t see his receipt but he kept telling me I was great and to keep the change so I can assume he was being legit. I honestly wouldn’t call it dumb, just bizarre. It made me wonder if he signed cashier names the entire time. Thank goodness the card companies never check those things.


#10 Difficult Parking

Someone once asked me something like, "Why are you guys making it so difficult to find a car parking spot this time of year?!" It was right around Christmas time and I was just a casual employee working in a tiny store nestled in a huge shopping center. I honestly didn't even know what to say to that person.


#11 Brighten the Room

I remember one time when someone asked, “Can we open the curtains to make the screen brighter?” (She asked this while pointing at a projector and screen setup.) Somehow, she legitimately thought that more light in the room would make everything brighter as if the projection was some sort of moving painting or something.


#12 Allergic Reaction

I used to work in an optician's office where we'd carry out pressure tests (a few puffs of air onto the surface of your eye) where quite literally, the machine just blows your eye with air. The customer was adamant that she was allergic to it and couldn't have it done. In fact, she accused me of not knowing what I was talking about.


#13 Bank Donations

I used to work as a bank teller. A lady came up to me and asked to withdraw money. I informed her that she couldn't withdraw money because her account was overdrawn. She was immediately upset, so I had her account checked for fraud. She then explained that all those charges were hers and she wasn't expecting any payments. She was spending money she knew she didn't have. She then asked me why we couldn't just give her more money.


#14 French Connection

I work in a bank and once had a pair of women come in. One said that the other was visiting from France and needed to check how much was in her account and asked if I could tell her. I asked if she was a customer of our bank (thinking maybe she was a student learning English and set up an account because that's quite common). But no, she wanted me to tell her the balance in her French bank account.


#15 Do I Have the Right Number?

Whenever I answer the phone at my workplace, I have to say, “Good morning/afternoon” and then our hotel name. So many people interrupted me halfway through this to ask if they called the correct hotel. Some people even asked me if they had called the right hotel literally just after I just said the name of it.


#16 That Won’t Work

I get too many dumb questions to remember them all. When sending confidential documentation, we would encrypt it and put a password on it. It's common practice to send the document and the password in two separate emails. I got a message from this guy saying he couldn't open the document I sent him.

I asked if he used the password, but he said there was an error. So, I asked him what password he used and he told me, “I just hit ‘OK’ and it said that I had the wrong password." I replied, “Wait… did you type anything in?” and he just went, “Well, no.” I then asked, “Could you use the password that we provided you?" He responded, "I didn't think it would work, so I deleted the email."


#17 Power Button

One of my users came today with an iPad. When I asked what the problem was, she said that when she held the power and home buttons for 10 seconds, it just shut off and took a minute to restart. That was her whole problem — if she held down the power button, it turned off. Unbelievably enough, she called it the power button.


#18 Is It Real?

I used to work at a fine jewelry kiosk in a mall. Our jewelry included items like gold bracelets and necklaces bonded with Sterling silver, Sterling silver rings with cubic zirconia gems, etc. I had a lot of regulars and this one woman would come in often. For every item she was interested in, she’d ask, “Is this real?”

I explained to her what “bonded” meant and how we didn’t sell diamond rings for $25. However, I added that the rings were indeed certified Sterling silver with synthetic gems. I gave her information like this over and over again, day after day, and she would follow up every explanation with, “Okay, but… is it real?”


#19 Hardwire the Problem

While stationed in Italy in the Navy, a "higher up" (E7) in the IT department came to us to ask why our ship's Satcom (satellite communications) was offline. We told him that it was nothing more than a connectivity problem and it would be up shortly. He then proceeded to ask why we couldn’t just hardwire it via Ethernet.

Trident Juncture 2018Navylive

#20 Open and Shut Case

I used to work in computer sales and repairs. I had a customer, who was maybe 23 years old, saying she couldn't get her laptop to open something. So I took it, opened it and casually asked, "What is it you can't get open?" She looked at me, shocked as I opened the laptop screen, and said, “I’ve been trying to do that for hours. How’d you get it to open?!” I looked at her, not knowing how to respond, and did it again. She took it and walked out, saying thank you. I took a long look at my computer I was working on and decided that this was the moment that made me quit that job.


#21 Salad Sauce

I work at an Italian restaurant and this guy was looking at ordering a salad. When I asked what dressing he wanted, he kept going back to the pasta sauces and asking, “Sugo. That would be good on it, wouldn’t it! I’ll get that” I tried to explain, “Sir, those are for the pastas. You got the Mediterranean salad” and he responded, “You’re right. Maybe carbonara.” I didn’t get what he wasn’t understanding. He seemed like a normal smart dude, but just couldn’t comprehend the difference between dressings and sauces.


#22 How’s That Possible?

I work at an independent pet store. We sell mostly dog supplies, but there's a small section of cat toys. A newer, pretty gimmicky item we brought in is a line of catnip that is packaged to look like… medical lettuce if you catch my drift. There're the 'prescription' bottles and pre-rolled stuff. Now, people know these are catnip products, but I've had multiple people ask, “But, how does the cat smoke it?" Or, "How can they even hold the lighter, they've got paws." I never quite know how to reply besides muddled laughter.


#23 Geometry of a Circle

A full-grown woman asked me how big our pizzas were. I stuck out my fingers, eyeballed about a foot and said, “A foot, so that big.” She paused for a moment and finally said, “Oh, lengthwise?” Our pizzas are circular. So, any point across is “lengthwise.” Maybe she didn’t know our pizzas were circular, but it was pretty dumb.

I went back to tell the other co-worker what I just experienced. Right after I told her the punchline she stared at me with this confused look on her face. She smiled and finally said, “Okay, not all of us are Mr. Engineer Student over here!” I just walked away. I didn’t know how to handle it. I’m not a genius for knowing about the geometry of a circle.


#24 Island Living

I was a driver in Honolulu. I once picked up a couple that was on their honeymoon from England. After about 20 minutes, the woman said to me, “So, we’re on an island right?” I honestly thought that she was joking until the husband started saying, “What the heck do you think we’ve been flying over the last day?”


#25 A Good Laugh

I used to work in a restaurant that was quite popular with the healthy lifestyle crowd. This particular lady asked me if we tested our water for ionizing radiation and made it clear that if we didn't, she would leave. Out of sinister curiosity, I told her, "Of course we do. In fact, I'll test it right in front of you, just let me get my Geiger counter from the back.”

I downloaded a mock Geiger counter app and tested a glass of tap water in front of her. She completely bought it and proceeded to order a fruit salad and a water bottle. To be fair, my phone case at the time made it look a bit blocky, so there's that. I told the manager and we had a good laugh. I still can't believe I got away with it.


#26 Those Little White Things

I worked at a Mongolian restaurant that served white rice. A guest honestly did not know what rice was when I offered him some. I had to explain it as "those little white things.” After 10 seconds of me trying to figure out if he was just messing with me, he looked at me still confused. I just said, “Nevermind” and dropped it.


#27 New Port

I was working at a college, trying to get a laser connected via the network. But the way they have it set up, we need admin rights to access the settings. I sent an email to IT asking them to open the port to us so we could configure the connection. An hour later, a dude walked into the class with a bunch of hardware and asked, “Where did you need the new port?"


#28 Before or After?

I’m a PI. I was investigating a case and I found an old couple who were friends of the victim. He would also occasionally come over to their house. I asked them when the last time the victim came over and they spent about five minutes arguing back and forth with each other whether it was before or after the crime took place…


#29 Turn Down the Volume

I work with fire alarms. I was once asked, "Is there a volume button to make it not as loud?" Not a stupid question, but there isn't. “Yes there is! You’re doing this on purpose! Turn the volume down or I’ll sue you!” I then told her to get away from me and she turned me in for being rude. Nothing happened to me.


#30 I’ll Go Elsewhere

I work at a gas station. A man walked up and stated, "Red 100s" at me. He clearly meant cigarettes, but almost every brand has a “Red 100s” version, so I asked him which kind he wanted. He repeated, "Red 100s.” I asked him if he wanted Marlboro Red 100s, Pall Mall, Newport, etc. He turned around and said if I didn’t know what reds were, he would take his business elsewhere. He did actually leave the store right then…. with all the different Red 100s just sitting behind me.


#31 Is This Covered?

I had someone ask why I sent them an invoice. I work for an accounting firm. We did a project for them, wrapped it up, and billed it. A few months later, they came back with another project. So we did the work and gave them a bill. They somehow thought that the new project was covered under the previous invoice.


#32 It’s the Combo Guy

I worked at Wendy's. One day, a man in his 50s wearing a bright magenta suit, walked in and ordered a burger. I asked, "Do you want a combo or just the sandwich?" He asked, "What’s a combo?" So, I explained to him that it was a sandwich with fries and a drink, but somehow he didn't understand. He looked at me blankly and asked, "I want fries and a drink, but what is the combo?"

We went back and forth on this for five minutes. I don't even remember if he ever got what a combo was or if he ended up getting it. I do remember, however, that I saw him two weeks later in a different city at my other job training political canvassers. He was wearing the same magenta suit. I was in such shock that I just stared at him, saying nothing, thinking, "It's the combo guy."


#33 Free Weefee

In high school, I worked at a Tim Hortons and we were advertising that we had just put in free Wi-Fi. An old guy at the drive-thru asked for a free "weefee.” We asked him again and he repeated himself. It wasn't for a few seconds until we realized he didn't know what Wi-Fi was and thought it was some sort of free promotional item. Maybe not necessarily dumb on his part, but it was really funny and turned into an inside joke at the store.


#34 Partying All Night

I worked at a small fine dining steakhouse in high school. The restaurant closed at 10:00 p.m. and one day, a table decided to take their sweet time with everything. So, it was 12:30 a.m. and I still had homework to finish and school the next day. One loser at the table asked, “Man, I bet you really want us to get outta here don’t you?” Ya no kidding, but I couldn’t tell him I did.

Instead, I told him, “Well, while I have to go to school in six hours, providing good service means treating every customer as if they’re your first one of the night.” Unfortunately, I shot myself in the foot right there. They didn’t leave until almost two in the morning and I was fairly late to school the next day.


#35 Park Ranger

My dad was a park ranger and he had many hilarious stories. The best was when he was just starting out at the Grand Canyon. He hadn't learned the finer points of customer service nor the depths of people’s stupidity yet. A visitor made a comment on a ranger-led tour. “The Grand Canyon must have made a tremendous noise when it popped open!” Dad said, “Yeah? Imagine the noise it’ll make when it slams shut!” The visitor was not amused.

Grand Canyon National Park: International Dark Sky Park CertificFlickr

#36 None of Your Business

I worked at a coffee shop where we sold two sizes: small and large. I was working the register, ringing up a girl. I asked her what kind of coffee she got, which went fine, but when I asked “small or large?” she responded with a suspicious, “Why do you need to know?” Are you kidding me? Because one is a larger quantity than the other and you pay for that extra amount. When I told her as much, she scoffed and grudgingly told me. Like, do you think I’m tricking you?


#37 One of Those Moments

A client came in to get an estimate for a canine neuter. He said, "So, he won't pee anymore after the surgery?" It was one of the rare moments in my life when my mind went completely blank and my eyes might have crossed. I thought I knew where he was going with it, but I just didn't want to believe it. This 45-year-old man thought that’s where urine was held.


#38 The Way to the Internet

"I have to have a computer to use the internet?" I received this question at least twice when I worked as ISP tech support for a telephone company back in 1999. Come to find out that the sales department was signing phone customers up for DSL, without either explaining what it was or asking if the person had a computer.


#39 Overtime Hours

I'm in the army. We had a long field event, about a month in the field, no showers, MREs, sweating in the south heat in August. Just a real awful time. I had a private ask me if we got overtime because we didn’t get to go home. I told him no, but he thought I was joking. My platoon sergeant blew up on the poor kid when he said he needed to go to finance because he didn't get his overtime.


#40 Volcano Roll

I worked at a Japanese place for a while when I was in college. We had this thing called a Volcano roll that cost $7.25. A California roll there cost $3.75. The Volcano roll was a Cali roll cut into the shape of a triangle and topped with spicy mayo that was heated up with about $.10 worth of fish. You’re much better off ordering a Cali roll and paying $.50 extra for spicy mayo on the side and asking us to heat it up.

I had one guy come in with a girl and he ordered a couple of regular rolls along with a Volcano roll. When served in the restaurant, unless they ask us, we would put the sauce on top so it looked nice. When I brought that roll over he was like, "Oh. I didn't know you guys put the sauce on. I've only gotten it for pick up and the sauce is always on the side. I don't really like it, could you bring me one without it?"

I tried not to laugh and said sure. I went back and the sushi chef asked what was wrong. I told him that he didn't like the sauce and wanted a roll without it. He laughed and said alright. So, he took a California roll, cut it up, and put it on the plate. I brought it back to the guy and he was super pumped about it.

Basically, this guy paid $7.25 for a roll that would have cost him $3.75. Me and the sushi chef got to split a free volcano roll. Normally, I would have just told him about it, but the dude was being pretty arrogant the entire time. I'm guessing it was so he could act like he was a sushi expert to impress the girl he was with.


#41 Limited Time Only

I used to work at McDonald's and when the chicken tenders first came out, my place sold out of them within two or three days. A customer tried ordering them after the fact and I told her we were sold out until the next delivery came in. She asked how we were out of chicken tenders in an accusatory tone as if we were hiding them from her. Like wow, a new item and a limited supply… I wonder how we're sold out?


#42 Getting Her Feet Wet

When I worked in housekeeping, I mainly cleaned porches and decks. One day, a woman who looked like she was just itching to talk to my manager came up to me and said, “The grass is wet.” This was because the sprinklers were going earlier that morning. So, in a polite way, I basically went, “So?” She then asked me to dry the grass for her so she wouldn't get her feet wet. I was so stunned that I just said it was 30 degrees Celsius out, so it would dry in 30 minutes.


#43 Point Me to the Bagels

I worked at a bagel shop. "Bagel" was literally in the name of the shop. Our logos were bagels. The wall painting outside, next to the main door, was of coffee and bagels. The window decorations were bagels and coffee. Inside, there was a bagel display case right in front of the main entrance. A woman once walked in with her kids. “Do you guys sell bagels here?”


#44 Four Milkshakes

One guy ordered four milkshakes: three chocolate and one strawberry. They came in clear cups and were marked clearly on the lid. We put “CS” for the chocolate shakes and “SS” for the strawberry ones. He looked at me and asked, “Which one is the strawberry one?" I gave him the benefit of doubt, thinking he may be colorblind. However, the strawberry shake had huge chunks of strawberry in it as well. And, again, they were marked.


#45 That One Book

I recently got a call at the bookstore I work at. The man asked me if I could find a book for him, which is pretty routine. I asked the title and he didn’t know. I asked the author and he wasn’t sure. What he told me is that he was in the store a few months ago and there was a display stack of "bluish-green" books that were going for about five or eight dollars. He wanted to know if we still had any in stock. I told him we undoubtedly have a variety of books that match that description if that's all he needed. He got very irate that I couldn't pinpoint the exact item he was looking for.


#46 Two Copies

Supplier said we needed two copies of a signed document to go ahead and proceed with the order. One sent to her requesting it and one to an upper-level manager. So, instead of me CCing both her and the upper-level manager with the attached signed document, she sent the same file twice in the email. It was for us to forward one signed copy to her and another to her manager. I replied with the signed document and CC'd her manager so he could read that bit of brilliance.


#47 Settlement Check

I’m a personal injury paralegal. A client’s settlement check came in, so I called to tell him he could come get it because I knew he wanted it immediately. He legitimately asked me if I could fax it to him. I thought he was joking. He wasn't. I had to spend about 15 minutes explaining why his plan wouldn't work.


#48 Get Rid of It

I did some freelance graphic design for a company that buys and sells properties. I would tidy up pictures for them of the inside and outside of the buildings. I once got a picture of a property where you could only see half of the building. My boss asked, "Can you just Photoshop out that building in the foreground?"


#49 Can You Read?

I used to work in a school library. We would open it for students during lunch, close the doors and put out a large closed sign when it got full. I mean a large, wheeled easel that the students could read from a ways down the hallway and had to walk around as it literally took up half the hallway. Needless to say, students would walk past this sign that says “LIBRARY CLOSED” and then try to walk in. My favorite response was, "Did you read the sign?" "No." "Oh, well if you can't read, you shouldn't be in a library. Goodbye!"


#50 Printing Yellow

I had a conversation with a woman about picking ink for a printer she just got. The conversation kept getting more and more ridiculous and I realized she’d never owned or probably even used a printer. At one point, she asked me this gem: “What order do I put the cartridges in if I want to print in yellow?” “Ma’am what do you mean?” “Well if I put the black cartilage in first, then where do you put the yellow one? Don’t I have to take all the other carriages out and just leave the yellow one if I want to print in yellow?”



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