30 Awkward Job Interviews That Left Applicants And Employees Losing Sleep

I was interviewing for a cashier job at Target. This was shortly after I had just gotten dentures.

During the interview, the manager asked a question, and while answering him, I felt a sneeze coming on. I held up a finger, indicating I would need just a second, grabbed a tissue, and sneezed…

Unfortunately, I didn’t have enough adhesive on my top plate, so when I sneezed, my teeth flew out of my mouth, across his desk and right into his lap.

This poor man completely lost it. He laughed so hard he was sobbing before he could contain himself.

It could have ended worse. He did hire me, and told me, “You’ll be great for comedy relief, if nothing else.”

I don't drink. I'm an alcoholic but don't advertise the fact, just say "No, thanks" when offered, and I've hardly ever had a problem with that.

Except for an interview I had for an anthropology job with the owner of an archaeological firm. It was a dinner interview at a Mexican restaurant with him and others from the firm in Shreveport, LA, and he kept insisting that I have a beer with dinner. Each time, each insistence got a little less jokey and a little more forceful. Once he asked me why, but screw him, I didn't owe him an explanation. That was the only time in the evening that I really felt awkward.

Eventually, he said that he couldn't trust a man who wouldn't have a drink with him. I told him that I didn't want to waste any more of his time then and left.

It didn't hurt my feelings or anything, just made me pissed off about the wasted time, and embarrassed for the other people at the table. I'm glad I found out early on that he was an a*****e, though. I've had it confirmed from others since then.

Many years ago, before the proliferation of cellphones, I interviewed a candidate for a Quality Assurance Engineer position. The candidate arrived a little late and was brought into my office. He politely asked if he could use my phone to make a quick call. I obliged and gave him the phone and told him to dial “9“ for an outside line. This smart, clever candidate called his boss to tell him that he is not feeling well and won’t be coming in today. This phone call was made with me sitting at my desk right in front of him.

I terminated the interview right then. Fortunately, he gave me clear examples of his loyalty, honesty and his decision-making ability. Usually, this can take months to reveal. Needless to say, he didn’t get the job.

I hadn’t been for an interview for a while, so the clothes I had to wear were a few years old. I had put on a bit of weight in the meantime, so the blouse I wore was a bit stretched across the breast area. Still totally wearable though.

I use my hands a lot when talking. During the interview I must have brushed across the blouse with my hands, because all of a sudden I noticed the man interviewing me had a look of horror on his face. He was fixated on my breasts.

I’m well past the age when men stare at my breasts. So, I looked down to see what the problem was. The button in the middle of my breasts had come undone. My rather ample bosom was joining in the interview.

I had no idea what to do. I continued talking and did up the button. I didn’t apologise, or comment on it at all. Not normally one to be at a loss for words, this was one occasion when I just couldn’t come up with something to say.

I got the job.

Back in college, at the end of what was genuinely a decent interview, I stood up and reached out my arms to hug the two interviewers. (To this day I have no idea why I tried to hug them).

They stared me down, which stopped me before I could actually hug them, while the woman on the left slowly but firmly said, "we... don't do that here."

I was mortified. Still kinda am, haha.

I called my interviewer "Mom" in my first job interview.

I’m an awkward person, so every job interview I’ve ever had has been awkward.

But I’ll tell you about the most awkward.

It was seven years ago, and I had returned from Japan just a month prior. I had posted my resume and was contacted by a recruiting firm that specialized in Japanese speaking jobs. The position was advertised as Office Manager (it wasn’t, but that’s a different story) in a company 20 minutes from home. I was so nervous that my Japanese wouldn’t be good enough, that they would notice my seven-month- pregnant belly and dismiss me, worried about my lack of experience in an office setting. Still, they invited me in for an interview, so the recruiter must have vouched for me.

On the morning of the interview, it was raining. Not refreshing summer rain, not even cats-and-dogs rain, but torrential, can’t-see-2-feet-ahead-of-you-why-are-these-windshield wipers-so-useless rain. Add up the rain, the nervousness, the pregnant belly, and the fact that I hadn’t gotten used to driving on the right side of the road again, and we had a real issue on our hands. Luckily, my dad whom I was living with, offered to drive and wait in the car during the interview.

We arrived too early, so I sat in the car and chatted with my dad to k**l a little time. Minutes later a Japanese man appeared at the door, opened up an umbrella, and jogged out to the car. Uh-what? My dad put the window down, and the man happily urged us BOTH to come in. My dad gave one of those little hand waves and mumbled something about “I’ll wait here,” but the man absolutely insisted he come in as well. We shrugged and ran through the rainy parking lot and into the building.

My dad took a seat in the foyer. Well, he tried to take a seat in the foyer. But again, the man insisted he come with us into the conference room. That man turned out to be the president of the company, and that turned out to be, hands-down, the most awkward interview I ever had- the president, two managers, me, AND MY DAD. I think the whole time the managers were wondering “why the hell is this guy here?” but they didn’t question their Japanese boss.

I got the job, by the way, so naturally, my dad takes credit for it.

I was asked ‘Why did you apply for this job, when you have no experience in the department you will work in?. My reply was ‘Why are you interviewing someone for a job they have no experience of?’ Luckily, it caused a laugh amongst the interview panel and it was agreed that I be given a trial. I suspect that I was the only candidate. If someone better qualified came along, I could be move into another area more suited to me.

The interviewer at the end of the interview asked me to take off my shoes and socks so he could see my bare feet. I asked him why and he said it was for the job.

I felt uncomfortable as I slipped off my dress shoes and peeled off my socks exposing my tan bare feet.

I remember looking at his reaction with a big smile saying nice…very nice. He asked me if he could massage them and that’s when I split. I grabbed my shoes and socks and ran out of the building barefoot and into my car.

Our company was hiring a receptionist and I was conducting the job interview with a colleague.

We met a young woman and interviewed her. It was in the late 90’s. The woman seemed competent for the position and she was nice too. However, something was bothering me and I could feel my colleague felt the same way.

She had a nose piercing on her nostril, some kind of round black stone.

It was discreet but still impossible to miss.

As the interview went on, I couldn’t help but wonder how this person would go to a job interview with a piercing on her face. It was an absolute faux pas and I couldn’t get past it. I personally didn’t mind the piercing in itself, I just couldn’t fathom how someone would make such a mistake, mostly for a receptionist position where she would be the face of the company, so to speak.

Finally, at the end of the interview, I decided to address the matter openly. My colleague was about to do the same, as he later told me.

So I asked her: “The interview went fine and we will definitely consider you for the job, but let me ask you something: don’t you find it risky to go to a job interview with a piercing?”

She looked at me, puzzled.

“A piercing?”

I pointed at her face and said: “Don’t you have a piercing on your nose?”

She frowned and said: “That’s a mole.”

So that was an embarrassing thing I did during a job interview.

I’ve never had an awkward interview, but my husband has interviewed hundreds of people in his job and has told me several funny stories.

He had one man show up at an interview very sweaty and nervous. During the interview my husband kept smelling the obvious odor of what he thought was freshly passed gas, At one point during the interview, he asked the gentleman if he would like to take a restroom break. The man declined. When the interview was complete the man rose to shake my husband’s hand and then turned to leave. It was then that my husband noticed that the man he was interviewing had fully pooped his pants, as well as the office chair that he was sitting in. To avoid embarrassment, my husband wished him a nice day and the interviewee exited the office as if everything was fine. Needless to say the poor guy didn’t get the job, and the upholstered office chair had to be thrown out with the garbage!

This was for an internship at Morgan Stanley. I had got through to the interview round after clearing the first round written test. It was a coding interview (which I seemed to have forgotten and will be evident shortly.)

The very first question (which I should have been more prepared for) was ' Tell me about yourself '. Again let me remind you it was a coding interview and the dumb*ss that I am, ended this answer with "and I am not as good a coder as I would want to be", in reply to which the interviewer said '' Let us not underestimate ourselves.''.

This is where I should have kept quiet and waited for the next questions or maybe agreed with the interviewer. But this was not to be and I immediately replied back with 'We must also face reality'.

*Awkward silence* followed by a "Hmmm" by the interviewer made it very clear the direction is which the interview was to proceed.

It was as if I didn't want the internship (Let me assure I did want it). However, lessons have been learnt.
1) Be prepared for the usual expected questions.
2) Speak the appropriate amount . No less and more importantly no more.
3) Don't act over smart.
4) Sleep well before the interview.

Oh gosh. I am cringing already and I haven't even gotten to the story.

It has been my dream for years to work in a Japanese design conpany. In 2013, when my parents moved to Tokyo, I thought it was a wonderful opportunity to start looking for internships at design agencies. I sent out 100 emails, got 30 replies and 10 positive responses. Back then, I had been studying Japanese seriously for about one year and my Japanese level wasn't the best. I am so embarrassed looking back at the emails I sent out then!

In any case, a friendly and quirky designer responded and said I could come for an interview. I prepared what I was going to say, got my portfolio ready, memorized his name and even went to his building a day early so that I wouldn't get lost on the day.

It was a hot summer day in July and I wore a light blue flowery pants (looks better than it sounds) that i had just bought in Harajuku. I also wore strap high heel sandals. At the door, per Japanese culture, I took of my shoes. I don't think they had slippers so I felt a bit awkward in my bare feet.

The designer didn't speak a word of English, and my Japanese wasn't great either. There was a huge awkward silence as he motioned for me to sit down and show him my portfolio. We went though my work and thinking back, I think he just acted interested in politeness.

In Japanese, you rarely say “you”, and rather refer to the person you're speaking to by their name or title. Unfortunatelt for me, I was so stressed and nervous that I forgot his name, and it was super obvious. I couldn't talk my way around that! I was also shaking like a scared hamster.

After awkwardly explaining my work on broken Japanese, it was time to go. He was kind and showed me to the door. I bent over to put my shoes on again, but there was no seat to sit on and as they we're heeled shoes, I had a hard time. I bent down, and all of a sudden, RRRRIP. My pants tore. Right down the middle. Everyone in the office heard it. There was silence for a few seconds and then I quickly ran out of the door, half-heartedlt thanking the designer. I walked with my hand on my butt for a few meters until I walked into the first store I came across and bought the first pair of pants I saw.

Needless to say, I never heard back from the designer.

(The happy ending is that two years later, I landed two internships at famous Japanese design and advertising agencies, and I managed to achieve a level of working proficiency in Japanese! I also never wear strange pants and heels to interviews anymore.)

The one where the interviewer farted in front of me. Not kidding. It was all I could do to keep a straight face.

My very last question at the end of an interview at one of the largest investment banks was "what's your favorite pizza". I blanked out because I was running on fumes and needed to k**l time, but I guess it made me stand out because I got the job.

In the early days of the pandemic, my friends and I would log onto Zoom calls and have a beer, often using immature names. One time, I logged in as 'Mr. Pee Pee Poo Poo Pants.' A few days later, I had an interview with Deloitte. Changing your name in Zoom isn’t immediately obvious, and I mistakenly logged in as 'Mr. Pee Pee Poo Poo Pants' for the interview.

Needless to say, I did not get the job.

Last minute HR add an individual to my panel interview — turns out it was my ex. I was offered the job and if I accepted we’d have to formally disclose our previous relationship. Awkward because the reason we broke up — I found out that he was engaged to someone else during our relationship, who was his now wife.

Had a brief Zoom interview with a company that has a similarly named competitor.

I got invited to an in person interview. When the interviewer asked me if I knew the location, I said, yes! The one by X street.

She said half-jokingly, "Noooooo, that's X, that's a different company. You're apply to Y company"

I did get the job.

They asked me what is my current occupation, I said single. English is my 2nd language btw

Not after but during an interview. I was applying for a position as a research coordinator at a University Rheumatology department. The MD in charge of the program was interviewing me. During the interview he asked me how Iiked working at one of the clinics on my resume. Having completed a Masters in Heath administration not too long before this I gave a compare and contrast of the business model between the one, he was asking about and another clinic I where I had worked. I mentioned that I got an inside picture of the one he was asking about as I had dated the administrator for a time while I was there. He said, “Oh you mean XXX ?” I said “Yes”, at which point he says, “You know he died 6 months ago”. Needless to say, I was rather stunned to hear this and had no idea how to respond other than to ask how he had died. After all of that I did get the job but definitely the weirdest thing ever said to me in a job interview.