Job Interview Horror Stories: From Grueling To Cringeworthy

Landing a job interview often feels like the ultimate accomplishment when you’re in the middle of the dreaded job hunt. But soon after landing that interview, anxiety creeps in. If you’ve ever felt nervous or unprepared to interview for a job you so desperately needed, don’t worry. You are not alone.

Awkwardness Is All Part Of The Game

From awkward handshakes to companies with the most grueling interview processes to job interviews gone horribly awry, we’ve gathered up some stories that not only can be viewed as cautionary tales but will also hopefully make you feel better about your next interview. Just be sure to remain on your A-game at all times until after the interview, unlike the person in our first story.

High, My Name Is…

On a Reddit thread asking “How did your worst job interview go?” user “beanboxer” told readers the story of what happened when she applied for a receptionist job at a law office. One morning she was smoking a “funny cigarette” with her friends on the beach, knowing her interview wasn’t supposed to be until the next day. Suddenly, she got a call from the office informing her that the interview had been moved and was in two hours.

Although she was under the influence, beanboxer managed to go home and get ready for the interview. She arrived at the interview, still in her “state of mind” and wearing heels. That was clearly a poor choice, because not only did she manage to trip in front of the interviewer, but she was unable to have a coherent conversation with her. Beanboxer ends her story like this: “as I was leaving I complimented my interviewer on her hair and asked where she got it done. She replied with ‘it’s a hairpiece. I have cancer.’ I didn’t get hired.” Yikes!

I Was Working as a Waitress at a Cocktail Bar

Reddit user “LilaFaith” recounted the time she applied for a cocktail waitress position at a well-known casino on the east coast. This is her story: “At the interview they handed me a bra and a pair of panties and told me to go put them on and pretend to flirt with them to get them to buy a drink. Since cocktail waitresses at that casino wear dresses and drinks are free for gamblers, I passed on that job.”

We think Lila was right to leave that job interview right then and there because that seems like an environment for sexual harassment. She noted that this must have been normal for the interview process because other applicants for the position did as they were asked, but she didn’t see why they didn’t just ask her to try on the actual uniform.

Wrong Place at the Wrong Time?

On a similar Reddit thread, user “jbartlet827” shared his experience which evidently was so terrible, he had to share it on multiple forums. They went into the office to apply or interview for a specific desk job, but when they got there the receptionist apparently didn’t understand why they were there, so they sent them into a different interview. When bartlet was in there, they were met with a panel of interviewers, who asked a series of questions bartlet did not understand.

For 45 minutes he answered “I don’t know” to all the questions, but luckily the interviewers didn’t give him a hard time about it. Knowing they blew the interview anyway, they still got their rejection letter and it wasn’t until then that they realized they were being interviewed for the wrong job — not the one they applied for. Cue the facepalm.

This Is a Test

Alyson Shontell, who is the Editor-in-Chief of Business Insider U.S., contributed to the “Tech Insider” section with her experience interviewing for Google as a hopeful college senior. After sending in her cover letter and resume, she received an interview request from Google, immediately being asked her GPA (she deemed her 3.5 as inferior for Google standards) and if she had any other pending job offers (she did not). Still hopeful, Shontell prepared for her phone interviews by researching every aspect of Google that she possibly could.

She was super confident going into her first phone call, until the interviewer said, “I’m going to ask you a few questions that may sound strange…These questions are meant to test your analytical thinking.” She was asked how much money she thought Google made from Gmail ads on a daily basis. Unfortunately, all her research proved fruitless, since she ended up confusing her interviewer. She had a subsequent phone interview after, in which the interviewer asked her a math question, over which she panicked, and ended with the interviewer giving her the correct answer. If you think that’s tough, Google is infamous for having even more intimidating interview processes, as you will see in the next slide…

Google’s Perplexing Questions

As you may have already guessed, Google is one company that has quite the interview process. They are most known for the incredibly difficult questions that they ask their candidates. Some of the questions include “How much should you charge to wash all the windows in Seattle?” and “How many golf balls can fit in a school bus?” If you are fortunate enough to pass the phone screening and make it to the in-person interviews (which is when they ask you these insane questions), you still have to stand out against the hundreds of other applicants that want the same job. There are at least eight screening processes before they actually make a job offer.

On their site today Google says that they receive millions of resumes each year, making it clear why the interview process is the way it is. Luckily, they now provide their own tips at how to properly prepare for applying and interviewing — and supposedly they’ve gotten rid of the ridiculously hard brainteasers. While Google has its insane questions, the next company has an interview process that takes a whole day!

My Day with Microsoft

Utsav Pandey, who is a Software Engineer at Microsoft, recounted what he went through to get into Microsoft’s offices on his blog After deciding to apply to technology giants, Pandey was contacted by a Microsoft representatives, who helped him get his first interviews scheduled. The first two interviews happened over the phone and during his first call, he was already asked to solve a question within the hour. After that first phone call, he received a call from an engineer on the team that was interested in him and was asked to work through a coding question.

After successfully passing those tests, he was invited to the Microsoft campus where he had a series of at least three on-site interviews with different people from the engineering team he was to work for. Of course, he was asked to code at all three. If he did well at the first three interviews — which he did — he moved on to two final interviews with senior members of the team. His interviews started at 11 AM and he didn’t leave until 7:30 that night! Talk about a test. Pandey did end up accepting an offer there, so he must have really known his stuff! The next company has a similar interview process but seems even more difficult to get hired at..

Amazon’s High Standards

Amazon, which is also in Washington state, has a notoriously difficult hiring process, according to Business Insider. The company’s founder and CEO Jeff Bezos has reportedly said, “I’d rather interview 50 people and not hire anyone than hire the wrong person.” Amazon wants each new employee to increase productivity and this way, company standards get higher and higher. So with each new employee, do the interviews get harder?

Jay Huang, who is a Vancouver-based freelance web developer, took to his blog to recount his experience in interviewing for Amazon. The interview started with the standard initial phone interview. He knew from colleagues that there should be a few phone interviews before getting offered on-site interviews, but he got invited to Washington after the first call. There, he went through seven different interviews, at which he was asked to talk through algorithms and do some coding. For tech companies like these, they do need you to really know what you’re doing but they also invite you over to see if you’d be a good fit for their team. In that case, you certainly wouldn’t want to mess up in the way this next person did..

Watch the Hair!

When Buzzfeed asked users to share their terrible interview experiences, “janetm48a5e179b” told the story of what happened when she went to interview for a grocery store. Her interview was held in an office on the second floor and as the interview ended, the interviewer walked her downstairs.

What happened next can only properly be explained in Janet’s words: “Being the clutz that I am, I tripped walking downstairs. On my way down, I grabbed the interviewer lady’s hair (hard) to try to help myself. I pulled her all the way down with me and we both tumbled down a few stairs.” But that doesn’t compare to the painful disaster on the next slide…

All I Want for Christmas Are My Two Front Teeth

On The Guardian, user “1scamp” shared his experience when he applied for work at an IT company. He had already gone through two successful interviews before he was asked to lunch with a secretary, while the interviewers discussed his application with the chief executive.

After his lunch, he was scheduled to meet with the chief executive and was feeling nervous, but confident. But it went all downhill from there: “I walked into the chief executive’s office. ‘Great to see you.’ I pulled up a chair but released the height mechanism by accident. The chair flew up and hit me in the mouth, knocking out my two front teeth. There was blood everywhere.” Ouch! If that’s not awkward enough for you, wait until you read the next one…

The Bathroom Encounter

User “raising hellions” told what happened when she got to an interview early. Since she was early, she went to the bathroom to touch up her makeup. While she’s in there, another woman walks in and they make eye contact before the woman walks into a stall. Suddenly, “hellions” hears the most disgusting sounds coming from the woman in the stall. She scurries to gather all her stuff and get out of there, but not before she smelled the putrid smell that followed the sounds.

Then, “hellions” says this: “Guess who was my interviewer? Both of us almost died when I was shown into the room. It was the most awkward interview ever. She… could barely even speak out of embarrassment… At one point the colleague had to take over because she just. couldn’t. even.” The next story has a similar bathroom-related embarrassment.

When Auto-Correct Fails You

The Muse asked readers to share their job interview moments and one reader was so excited for a non-profit she had just interviewed for, they decided to email the executive director a quick follow-up thank you note. The first mistake was deciding to do that from their phone.

Here’s why: “While I thought I wrote ‘I can hardly contain my excitement about the possibility of working with your organization,’ auto-correct changed ‘excitement’ to ‘excrement.'” The reader promptly called the executive director to explain the mishap and luckily she was so amused, that they remained connected even though they didn’t end up getting the job. At least that interviewer had a sense of humor, unlike the interviewer in the next slide.

The Recruiter Who Yelled

A man named Todd shared his story with Todd, who had previously held executive positions, was applying for another such position when an “executive recruiter” sent him a questionnaire that was ten pages long. Todd only completed half before sending it back, because he felt that considering what position he was in, talking about his resume was more important.

When he arrived at the interview with the recruiter, the recruiter threw the half-complete questionnaire on the table and began to yell at Todd! Because he didn’t finish it, the recruiter called Todd a loser with no future. Todd got up to leave saying he made a mistake, but not before the recruiter called him a…well, a mean name. If Todd was truly interested in the job, he should have completed the entire application, but that doesn’t mean he should be berated by a recruiter. Some people are just unsympathetic and do not understand how to deal with people, like the recruiter in the next slide.

Location Discrimination?

User “kcunning” contributed her job interview experience to, starting off by saying that the interview had initially gone well. She even met the woman who would be her boss and who wanted her to work there. That’s when the recruiter asked where kcunning lived, which was about an hour away from the office in a town that was considered lower class.

The recruiter asked her if she would move close to work, but she said she was fine with where she lived. The recruiter pressed on, asking about the commute, but kcunning didn’t mind. The recruiter then asked, “You’re married. Doesn’t your husband make enough for you to live out here?” To which she gritted her teeth and replied, “His salary isn’t your problem either.” She ended up not getting the job, probably because of where she chose to live.

Trying to Work at Facebook?

Facebook is another company that is known to have an intimidating interview process. Business Insider asked Facebook’s global head of recruiting, Miranda Kalinowski, what exactly the process is like. There is typically one screening phone interview and then subsequent technical interviews, depending on the job for which you are applying. The technical interviews are usually conducted by someone who is already in the position you’re applying for, since at that point the questions are focused more on the technicalities of that specific job.

If you pass these interviews with flying colors, you will be invited on-site to a third interview, where you get to tour the headquarters. They even give you a demo with their virtual reality headset to help you open up more. But it’s not all fun and games. Depending on which department you’re trying to go into, there’s an all-day round of interviews waiting for you. They will even try to ask you difficult questions to test your thinking and see how engaged and dedicated you are to the job and to the company’s growth.

McKinsey & Company

When determined the most difficult companies to interview for in 2013, McKinsey & Company was determined to be the hardest. Based out of New York City, the prestigious consulting firm conducts different forms of analysis in order to determine the best management decisions across public and private sectors.

Despite a difficulty rating of 3.9 out of 5, most interviewees have rated the grueling 39-day process as a positive one. Many candidates are asked to work through different work scenarios, in addition to simply just being interviewed. According to management consultant candidates “are asked to work through and solve a business case.” Sounds like a difficult task when you don’t even work there yet!

Go with the Flo

Progressive Insurance is also known to have a lengthy and extensive interview process that not only includes phone screenings and in-person interviews but background checks and tests to determine your skill set and personality. A personality test makes sense, considering the spokeswoman for Progressive has quite the personality herself!

Samantha Zupan, the director of corporate communications at, has offered her insight on why many companies have their difficult interview processes. Of Progressive, she said, “many candidates speak to the level of detail they are asked to provide about past experiences, as well as the many steps candidates have to go through as a part of the interview process.” Because a job interview process is so lengthy, that might indicate the care a company takes into its employees and its operations. It could be worse, as you will read in the next slide.

Thanks, But No Thanks


Reddit user “TBTurtles” took us back to 1994, when he interviewed for a graphic design job at a small firm. TB was well dressed and well prepared with his portfolio, arriving at 5:30 as the firm requested. To his shock, the interviewer turned out to be a total creep.

Here’s why: “The guy’s shirt is half undone, grey hair fuzzing out of the top and has dirty khakis. He pulls out a cigar and starts puffing and pours himself a scotch or something. I’m 25, sitting there thinking I need to nope out of there because alarm bells are going off. The office is empty and the lights above the cubes are dimmed so it’s super-creepy. He speaks nothing of the position and basically yammered on about how OJ may be crazy, but he didn’t kill his wife. I glanced around for exits and said thanks for the interview and got the hell out of there. I actually got a job offer the next day on the phone. When I said, “no thanks, he actually asked, “can I ask why not?” Dude.”

Please Hold


In a collection of horrible job interviews from Business Insider, one submission was actually from a recruiter, who was interviewing a potential attorney for his company. The interviewer noted how the woman was obviously full of herself, which is something a lot of interviewers don’t like.

This is what happened next: “Then her cell phone rang – she cut me off mid-sentence to answer the phone and then, instead of saying she would call back, began to have an extended conversation.” Needless to say, the recruiter left the room and decided that this woman would not be getting the job.

That Awkward Moment When…


If the previous stories weren’t bad enough, imagine what would happen if your interviewer began breaking down into tears! According to an article from, one submission was about someone who was in the middle of an interview, when someone notified the interviewer that they had an important call that had to be answered right away.

According to the submission: She picks up, and over the next 30 seconds she went from all-business, to horror, to breaking down in sobs and crying. Then she was helped from the room, with me sitting there wondering what the heck just happened. It turned out, that it was her doctor calling, to tell her that her husband had just died of a massive heart attack.”