Embarrassed People Share Their Most Awkward Job Interview Moments

November 19, 2019 | Nicholas Robert

Embarrassed People Share Their Most Awkward Job Interview Moments

Most people have been involved in the interview process at some point in their lives: whether as the interviewee or the interviewer. As the interviewee, the nerves are tingling, hands are sweating, and the mind is racing. Being interviewed can be tough, as one tends to overthink his or her answers, hoping to display their best selves in order to secure the position. Other the other hand, the interviewee faces the stress of finding the right fit for the job opening. Both the interviewee and the interviewer are under pressure, which is bound to lead to some awkward moments: some of which beg the question, “What the heck is wrong with you?” Let’s take a look at some of the cringiest moments in interview history.

1. Not the Best Hand to Lay Down

I once interviewed a candidate for an intermediate level analyst position. He bragged during the interview that he used to work other office jobs and play poker at the same time. This was in the late 2000s, while online poker was still in its boom. He bragged these things to me as if I, a relatively young professional at the time, would think he was cool.

Perhaps he thought it demonstrated his ability to multitask and still get his job done. I have no idea. Either way, we did not extend him an offer.

Awkward Job Interviews FactsWikimedia Commons, Santeri Viinamäki

2. Gettin’ Freaky

I had a candidate who came in and immediately said how hot my administrative assistant was—but then, it got worse. He asked if she was single or “Open to freaky Fridays.”

Awkward Job Interviews FactsFlickr, Amtec Photos

3. Draaamaaa

She listed all of her ex-boyfriends that currently worked there, and said she couldn’t wait to see the look on their faces when she showed up to work. This was in the first three minutes of the interview. I wasn’t even close to offering the job yet. I cut the interview right there and sent her on her way.

Awkward Job Interviews FactsShutterstock

4. A Blockbuster Move

I used to manage a Blockbuster. After one particularly awful interview, I walked the candidate out towards the parking lot, and the alarms went off. It turned out that he had stuffed three DVDs in his suit jacket before being called to the back office. He did not get the job: or Mamma Mia, Fool's Gold, or High School Musical 3: Senior Year, for that matter.

Awkward Job Interviews FactsFlickr

5. Hobo Secrets

I worked as a manager at an ice cream store in high school and staffed the store with other high schoolers. One day, a middle-aged man who was the epitome of a drifter—face tattoos, beat up leather clothes, and a big knife on his belt—came in and asked for an application. I obviously wasn't going to say “no,” so I handed him one. He proceeded to fill it out in store, and handed it in.

His previous work experience said it all. He’d worked in a liquor store for two weeks about ten years before. Reason for leaving? Got in a fight with his manager. His job before that: liquor store 14 years prior, lasted a week. Reason for leaving: fight with his manager. I told him that we weren't hiring right now, which we weren't, but that I would keep his application on file and would call him if something opened up.

Sadly, I never got to hire him and learn his secrets.

Awkward Job Interviews FactsFlickr, Amtec Photos

6. The Three Strikes

I interviewed a guy who in the interview did all three no-nos. First, he commented that I was a woman, and asked if I was, "Actually his boss, or just an HR desk clerk?" Second, he asked if we drug tested, and if so, could he take it in, "Like a week, because I should pass then." When I said that we are business casual, his response was, "Well, you will need to provide me with pants, since I only own jeans."

I didn't hire him. I am still baffled when I think of how bad of an applicant he was.

Awkward Job Interviews FactsNeedpix

7. Did He Get the Job?

I had someone show up in Daisy Duke shorts and cowboy boots for an office job at a four-star hotel.

Rest My Case factsShutterstock

8. It “Seamed” to Make Sense

I hire student (university) workers. One of my questions is: “Tell me about a time at work where you made a mistake, and how you fixed it.” This kid had no prior work experience, so I modified the question and removed the “at work” part. I thought he’d tell me about screwing up at school or at home. But no, he told me about the time where he ripped his pants in gym class in the fourth grade.

He didn’t tell me how he fixed, just that he ripped his pants. So, I’m assuming his pants are ripped to this day. This kid was a goldmine of what not to do in an interview. He did not get the job.

Awkward Job Interviews FactsPxHere

9. Yikes

A few years ago, I was hiring for a new graphic designer. The guy didn’t have much working experience and was a little odd, but I liked his portfolio, so I decided to interview him anyway. The whole interview was bizarre, but ended with the question “What do you think are your weaknesses?” He replied, “Ummm, to be honest, I have some pretty violent tendencies.”

No thanks.

Awkward Job Interviews FactsNeedpix

10. Call Him for Round Two!

I had a guy show up 40 minutes early for an interview, obviously crazy nervous. 30 minutes later, me and my team greet the guy, and you could tell by the fantastic handshake the nerves were still there, and that it was not going to go well. I motioned him to the board room to do the interview, we sat down, and before I had even asked the first question, he had barfed all over the table.

The funny thing was, he was one of the better applicants, so he did get a callback.

Fire Me, I Dare You factsGetty Images

11. “Why Did I Say That?”

I was an interviewee for a job in a record shop, very young and naive, just turned 19. They called me for a short phone interview and I did well enough for them to ask me to come in for a work trial the next day. I could have said, “I’m afraid I can’t attend that day; would it be possible to reschedule?” But nope. I don’t think well on my feet.

What I said instead was, “I can’t come in tomorrow because I’m working, but I can call in sick there if you like?” Surprisingly, I didn’t get it, the manager said he would call “another time to reschedule” and then I got a rejection letter a few days later. I still cringe when I think about that one!

Awkward Job Interviews FactsShutterstock

12. Got It All Wrong

Videogame testing is many people’s dream job, and we don't look for much at entry-level. If they are trainable and not a shmuck, that’s basically the bar. "Describe a scenario where an art bug is more important to fix than a crash," I asked the interviewee. Their reply? "Lara Croft's breasts are wrong." All I could say was: "Thanks for your time."

Awkward Job Interviews FactsFlickr

13. There’s the Door

I've only been part of the job interviewing process once, and this one applicant was a disaster. Right off the bat after she meets me and the business owner, she proceeds to make a joke about semen. The interview lasted two hours, ninety-percent of which was her telling us her life story. She swore multiple times. She used a racial slur when referring to one of the lecturers from the university we both attended.

On top of that, she interrupted me when I spoke. She also did not answer interview questions. She just kept talking about her childhood. She then told us about two people/organizations she is busy suing. Needless, to say, she did not get the job.

Retail Moments FactsShutterstock

14. That’s My Wife You’re Talkin’ About!

We were hiring for a process support role through a staffing agency earlier this year. The candidate comes in, we do the whole tell-me-about-yourself dance, and I dig in with some situational questions. One of the questions dealt with how they had handled joining a new team with strong, sometimes conflicting personalities.

Their reply: “Oh sure. I dealt with that before. You know, I’m not racist, BUT...” The candidate then proceeded to make racist comments about the ethnic group my wife is from. They didn’t get hired.

Awkward Job Interviews FactsPixabay

15. Sorry, You’re Not Tall Enough to Get on the Ride Called: Employed

Oh goodness, I had one girl where it seemed clear was only there because her parents wanted her to get a job. I'm sitting there, attempting to make conversation. I hire for a fast-casual restaurant, so it's not like I need their life story. It's nearly impossible for me to get this girl to have more than a one or two-word response. I'm to the point where I'm about to be done with this girl and just tell her to leave.

Then the store owner walks up to the table. She often sits in on interviews and asks questions that I don't think to ask. She walks up and introduces herself as the store owner, "Hello, my name is [redacted], how are you?" Her response? "Wow, you're tall."

Awkward Job Interviews FactsNeedpix

16. “Eh, Glad I Made It on Time.”

I went to hire a girl for a restaurant I was managing. She showed up for the interview and seemed really off, like she was on something or had had a few drinks. A short while later, the cops showed up asking who's badly damaged vehicle was in the parking lot and questioned some kitchen staff. That’s when things really got out of hand.

The next thing you know, she sees the cops and bolts to the bathroom. The police had to go in and grab her. When they searched her, they found a half-empty bottle of vodka and some pills of some sort. She was arrested and escorted out of the restaurant. Apparently, on her way to the interview, she sideswiped another vehicle.

Needless to say, we never saw her again.

Teacher Confiscated FactsShutterstock

17. Just Pickin’ Rocks

I was hiring for an entry-level cable tech position in a part of the state with a small candidate pool. A supervisor passed an applicant to me, saying he thought the guy had a good work ethic. I show up to the local office and find a place for our interview, letting the lady at the front desk know to be on the lookout for our applicant.

My first warning sign came when she came back to let me know he'd arrived. The first words from her mouth were: "Please tell me this guy won't be customer-facing." His resume was sparse, but since it was entry-level, I wasn't too worried about that. His work history only contained work at his family farm and a single season at a ski resort.

I'm from a state with a lot of farmers, and I've known them to be hardworking, so I don't think anything of the limited scope of his background or the jeans and collared shirt he'd worn to the interview. I ask him about his work on the farm, and what kind of things he usually did there. His reply was three words: "I pick rocks.” After a few moments when it became clear he wasn't going to elaborate on his own, I asked him what that meant more specifically.

He said that it was his job to walk alongside the till and pick up any large rocks it unearthed. "Okay, what else?" "Just the rocks." Trying to find somewhere for my line of questioning to go, I asked him what his favorite part of the work was, given how many years he'd been at it. His eyes squinted slightly as he gazed to the side, as though he was thinking very hard about the question, but was coming up empty-handed.

"That's okay," I said "it's easier for some folks to recall their least favorite part of the job. What's your least favorite part?" "Pickin' rocks."

Awkward Job Interviews FactsPixabay


18. Wait…But Which Movie?

I had a phone screen interview with a candidate for a software development job at a large internet retailer. For fun, let's say it was eBay. Some red flags during the interview: His resume was five pages long and obviously faked to game resume scanning programs. His "skills" section was a solid paragraph of every popular technology from the last 10 years.

I'm talking a brick-sized section of text. He answered the phone and I could barely hear him because he decided to have the interview at a Starbucks. He wouldn't stop talking, but he never said anything of any relevance. It honestly sounded like a used car salesman. He didn't have a computer ready. He didn't have a pencil or paper.

He couldn't answer any technical questions I asked him. He ended the phone screen after about 10 minutes because he had a movie to go see. My head was spinning after I hung up the phone.

Awkward Job Interviews FactsFree Stock Photos

19. A Girl’s Gotta’ Eat

I did not personally hold the interview, but I saw the whole thing as my manager left the door open. I worked at a ballroom dance studio. A girl was in for an interview about a dance teacher position. Partway through the interview, which was something like 15 minutes total, the girl’s mother comes in, goes over to the room, and hands the girl a bag of McDonald’s.

The girl does not skip a beat, or apologize for apparently needing to eat right at that moment, and goes on to pull out the food, set it up on the table, and eat while my manager is still trying to interview her. It looked so awkward. She did not get offered a second interview.

Awkward Job Interviews FactsFlickr

20. Yes, Yes You Do

This horror story was wrong on so many levels, easily one of the WORST experiences I've had in my working career, period. When I was working for a transport company, I was the “office girl”—which just meant that, if it wasn't out in the garage, I took care of it. This included initial interviews. So, we were looking for a loader—it's a simple job.

We get a resume online, I call the guy, ask when he can come in for an interview. Guy says, “Whatever works for you.” I say I can get him in on Monday. This was on a Friday. Strike one: guy says he has something going on Monday, what else do I got. He went from “Whatever works for you,” to, “No, not Monday.” But whatever, we need a loader.

I ask if he can come in on Tuesday instead. He says sure and asks what time, and what to wear. I tell him 9:00 AM, and that we're pretty casual—we're a trucking company, after all. He asks me to define “pretty casual.” Which is fine: I've had peeps tell me “business casual” and want dress clothes, or business professional and I show up and everybody's wearing shorts.

So, I tell him that he needs jeans, a sturdy pair of sneakers, although we prefer boots, and a clean shirt—no graphic designs, please. Pretty simple stuff. He comes in on Tuesday, at 9:10, wearing flipflops, shorts, and a band tee. I want to say it was Metallica, but it's been a while. Alright, so there's strike two, since I specifically told him none of the above when he asked, and confirmed the time.

But, sometimes people make mistakes. I ask him to come on in to the back with me and sit down, and we'll get started. He sits down, and then he asks when he can meet with the owner. I tell him that the owner is out. Then, he commits strike three: He asks what MY qualifications are. I'm a bit confused, so I ask him "Qualifications for what?" "To hire me, of course," he says, like it's oh-so-obvious.

"Are you asking if I have the authority to approve your hiring? If so, then the owner could change his mind, of course, but if our interview goes well, I can get you started tomorrow." He then says, "No, like...are you the HR person or just the secretary?" I politely inform him that, while the owner is on the road, I run the office.

He seems to be satisfied with this. So, I go over the job description, pay rate, what the hours typically look like. I ask is he is satisfied with this. He says he is okay with it until he is able to be promoted to driver, of course! I inform him that you can't be “promoted” to driver—that requires a specialized driver's license. He looks a bit disappointed.

I tell him that we're willing to hire him, on two conditions. One: he comes to work tomorrow dressed appropriately in jeans, sneakers, and a non-graphic tee, or sweatshirt. Two: he has to drive about 15 minutes away to go take a drug test. Guy legit thinks on this for a moment, and then says, "Do I have to pass the drug test?"

I didn't even say anything; I just stood and motioned him towards the door.

Whole Class Laughed FactsShutterstock

21. Mama’s Boy

A 28-year-old college graduate came in for an interview with his mother. I normally don't do the interviews except for when there are issues or my boss is out. The interview was for an engineer position that opened up, and we had a lot of applicants. At first, I noticed a lot of my co-workers laughing and thought they were trying to mess with me.

Anyway, I walk into the office, and there he was, sitting with his mother. I was completely stunned. Before I could even ask a question, the mother starts asking how much the position pays, vacation time, and some other off the wall questions about compensation. I explain that compensation and other benefits will be negotiated at a later time and she tells me that anything under 100K won't work and starts demanding days off next month.

I stopped the interview and told her, since the interview candidate, her son, had not even said a word, that this is over, and asked them to leave. I really thought someone put them up to it, but it was a real interview.

Awkward Job Interviews FactsShutterstock

22. Fun Times—Evidently

I have a friend who screens resumes as part of her job. She has some entertaining ones. Like the person who spelled the name of her previous company incorrectly. And the one who explained a chunk of jobless time as she was taking care of an ill family member and "evidently, he died." The best job application I've ever read? The guy concluded his cover letter with a GIF. We hired him.

Everyone Quit factsShutterstock

23. Let’s Try This Again

I was hiring for a maintenance position for a huge mid-level apartment complex. Sifting through 30 resumes a day. Most had just the worst layouts, bad spelling, no experience, the works. One guy sent me an email with NO message at all, just a "my resume" in the subject, with no attached resume. I sent him an email saying, "Haha, don't you hate when you forget the most important step! Send me the resume next chance you get and I'll check it out."

Return email, "Yeah, I did." I kid you not.


Awkward Job Interviews FactsPxHere

24. Some Parents’ Kids

I asked the guy I was interviewing “What do you know about our products?” He replied, “Nothing really.” So then I asked, “So why would you like to work here?” Then he says, “Oh, I don't really want to work here, I just have to get a job so I can keep living with my parents.” I was taken aback, and so I ended the interview. I couldn’t believe his next question.

He asked me: “So, when can I expect to hear from you?”

Still Mad About FactsShutterstock

25. Sup, Dude?

The day after Colorado legalized weed, I interviewed a guy over the phone who would be working onsite at one of our client offices out there. I call him up. When he picks up, there’s a five-second delay before he says hello. I ask if I had the right person, and he just said “huh?” I clarified who I was and where I was calling from.

He just kept saying “huh” and rustling around in a bag of chips. I kept asking if he had the time for the interview and he just kept repeating “this is Jeremy.” When I lost my patience, I thanked him for his time and said I’d be pursuing other candidates. That’s when he asked: “Yeah, okay, please let me know if I get the job.” I hung up on him.

Awkward Job Interviews FactsMax Pixel

26. “Ya’ll Hirin’?”

This guy poked his head in from off the street and yelled at me, "Ya'll have resumes for workin’?"

Weird Flex Kids FactsShutterstock

27. Face Smack

A friend of mine who is one of our two hiring reps at our store told this one about a girl she had to interview during our hiring season. When the girl came in she said, "Thanks for coming, and before we begin, just want to clarify, is it pronounced (TAHN-yuh) or ( TAN-yuh)?" The girl replied: “It's pronounced Tan-yuh, I punched a girl out when I was drunk at a club when she called me TAHN-yuh,” replied the interviewee.

Needless to say, she wasn't called back.

Awkward Job Interviews FactsShutterstock

28. Sorry, You Failed

A guy called me to inquire about the status of his application. He starts off with the most incredible opener: “Why the hell don’t you answer your damn phone? People are trying to get jobs.” Taken aback, I asked for his name. I found that he had failed his online assessments and we couldn’t bring him in. I had the pleasure of saying: “I’m sorry sir, but you failed your tests and are not qualified to work at Wal-Mart.”

He quickly hung up the phone without saying anything else.

Awkward Job Interviews FactsFree Stock Photos

29. Give The Guy a Break

I’m a researcher. Our spaces tend to be filled with random things. My office is decorated with various llama items. A lamp, framed art work, a few stuffed toys, etc. Friends and coworkers get me the items as they know I enjoy it and I tend to display them. A job candidate came and flopped down in a chair, takes a lazy look around and goes, “So, you like sheep, huh.”

He did not get the job.

Awkward Job Interviews FactsFlickr

30. Do You Have Any Special Skills?

"Tell me a bit about yourself." The reply?  "I'm really into hacky-sack."

Awkward Job Interviews FactsWikimedia Commons

Sources: Reddit,

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