Discuss: Interview 20 Questions

Jul 19, 2013

Earlier this week, I came across a Learnvest article about inappropriate job interview questions and how to answer them.  It got me thinking about the strangest interview questions that I’ve ever been asked.

I spent the bulk of my late teens and twenties competing in beauty pageants so I’ve been asked some doozies.  “What kind of tree would you be, and why?”  “Do you believe in ghosts?”  “Pretend your on QVC, how do you sell yourself to me?” Apparently, you can purchase my dignity for four Flex Pay payments of $29.95, but my life as a pageant contestant is another post.  Maybe another blog.  This is about job interview questions.

The strangest question a hiring manager ever asked me happened during an interview for a temp position at a local media firm.  It was summer semester and I was between jobs and thought a position buying commercial airtime for political campaigns would be a good learning experience.

After discussing my education and experience, the interviewer–a man who wore a gold bracelet with a chain so wide it could anchor a small boat–asked me, “Do you eat, or are you one of those women who’s on a diet all the time?”  (There was tray covered in stale-looking cookies out on the table, and he was curious why I was the only candidate who hadn’t eaten one.)

Taken completely aback and utterly mystified by how to answer, I told him that I hadn’t eaten a cookie because I wanted to be able to speak freely during the interview.  His response?  “I don’t trust women who don’t eat.”

Fast realizing that this wasn’t someone that I wanted to work for, I shot back with something to the effect of, “That’s interesting, because I don’t trust people who eat crumbly, flavorless cookies served on plastic trays.  I hope you find a man you think is qualified to have this job.  Have a nice day.”  I walked out so fast, I left a contrail behind me.  I don’t recommend this strategy, but I was younger, bolder and more reckless then.

A grad school acquaintance was hired for the temp position.  He quit after less than three weeks.  The man who interviewed me apparently liked to duck out of the office for hours at a time to play golf and run errands, handing all of his work off to the temporary hires and junior staff.  He would then alter the emails, logs and memos to look like he had done most of the work before putting them on the boss’s desk.  What a gem.

Lesson: If someone makes you uncomfortable in a job interview, this may not be the person or the company you want to work for.

So have you ladies ever been asked a strange question in an interview or felt like the interviewer was trying to trick you?  How did you handle the situation?  And if you hire people as part of your duties, what’s the strangest question you’ve ever asked a candidate?


share this post

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. C says:

    Rumor has it that Justice Scalia keeps a plate of (very messy) powdered donuts next to the chair for clerkship candidates. Those who don’t take one apparently are frowned upon for not being willing to take a risk.

  2. Sarah says:

    During an interview for a job that had nothing to do with food or beverage in any way, I was asked “If I take you to a bar and say to order whatever you like, what are you going to get?” I replied that I’d probably get a Jack & Coke, and got the job because I “didn’t give a stupid Lite Beer/Skinny Marg/Daquiri answer, you answered like a human with taste buds.” That man has become one of my best friends in life…not sure if the question mattered for the job as much as our friendship, but I’ll take it!

  3. A.B. says:

    At three separate job interviews when I first got to D.C. as a 22-year-old newlywed, I was asked why I was married. The first interview in which I was asked this question was by far the worst. When I gave an answer my interviewer did not find acceptable, she asked, “But didn’t you marry for love?” I tried to laugh it off and said of course, but I decided I’d be miserable working at any place where I was being judged for my personal choices.

  4. Elissa says:

    During an interview for a legal internship, the interviewer asked me basically what would I do if it became clear my boss wasn’t following the law (Idk how to phrase this but the question was like what if your boss was acting shady). My answer was that depending on how serious it was, I would, as tactfully as possible, confront my boss about it. I didn’t get the job. I’m still not sure what kind of answer they were looking for.

  5. A says:

    I once had a hiring attorney ask me if I was in a serious relationship because he didn’t like hiring young women who “just get married and then move to California.” I did not get the job and, in hindsight, that’s probably a good thing!

    • ac says:

      Sadly, I think I know what firm this was because I use to work there. And a lot of women did leave after getting married. This particular (senior) attorney would then bring this up nearly all the time. Nice guy though and actually very fair to the women he worked with. Of course, it would be sadder if this was a different firm.

  6. cj says:

    I walked into a panel interview, shook hands with the interviewers, and was immediately told “Tell me a joke.” The shock drove all jokes out of my head except a horrible dead baby joke from high school.

  7. K says:

    I was once asked to juggle (literally) during an interview. Apparently it was a hobby of a few other employees, and they wanted to see if I’d fit in. In the same interview, I was also asked what kind of animal I would be if I were an animal. I didn’t get the job.

    • SmallFry says:

      Not for a job, but I interviewed for an editorial position on my journal at my law school. Two questions I got were: “If you were and animal, which would you be?” (apparently there WAS one right answer). Also, if you could be and Disney princess, which would you be? Can’t imagine how they fielded that question to the male interviewees.

    • SmallFry says:


  8. Nancy says:

    I did not have any that were completely out of left field, but my dept head is infamous for asking inappropriate questions during an interview. He once asked an female job candidate if she had any questions ‘about any female issues’. best we could figure was he was asking if she had questions about the company maternity policy.

  9. Wj says:

    This one has still bothered me. Tell me if I’m crazy.

    I once arrived for an interview for a political job and was told we were going to go to a public coffee shop nearby to conduct the interview because office space was limited. When we got there, the café was very quiet, such that the dozen-or-so patrons there could all hear our table pretty well. Given where it was, it would be reasonable to guess they were all political employees of one stripe or another, or even reporters. The interviewer asked me to start describing my work with for a prior political job and I said, “I’m not comfortable being totally candid about my past projects here. Most of them weren’t super politically sensitive, but I would definitely describe them differently and in more detail if we were in a private setting.” Well, with not quite that much poise–because I was self-conscious even saying that! This didn’t seem to register as a big issue with her. She told me to just say as much as I could. The interview didn’t go well. I was second-guessing and self-censoring everything as I went. (To be fair, it might not have been a perfect match anyway.)

    I didn’t get the job. One possibility I’ve thought of is that they had already found someone they wanted, and my interview was already a formality.

    Even so. Even I were interviewing someone for a totally non-sensitive, non-political job, I’d avoid doing it in a public setting like that. Interviewees are already self-conscious the spot as it is.

    Has this happened to anyone else? Am I just being sensitive?

    • Belle says:

      I was in an interview where the person doing the hiring asked me questions about my old Boss that I didn’t feel comfortable answering. I told him that cong offices are like Vegas, what happens there, stays there, and if I couldn’t keep my old boss’s confidences, how could he expect me to keep his? They made me an offer, but the whole thing soured me on the office so I didn’t take it.

  10. anon says:

    I worked for a disgraced congressman and one person asked me if I had any idea/if he did anything to the male interns in our office. It was the strangest and most uncomfortable question.

  11. Sam says:

    During a particularly grueling interview by a panel of people with whom I would be working, one person asked if I was a loner. It was a terrible way of asking if I work well in groups, and after an hour and a half of being exhausted from a long line of similar questions, I repeated the question back to him and asked what he meant. I answered as best as I could, but the question threw me. I did not get the job, but after a question like that among similar questions, I didn’t care to work at that place anyway.

  12. Linda L says:

    Interviewing for the job I currently have, I was asked “if money were no object, what would be your ideal job?”. I didn’t think the answer should be “this one, of course!” Caught off guard, I answered truthfully – I’d want to run a doggie day care. I was kicking myself afterward because that had nothing to do with the job I was going for. But the hiring manager happened to be a dog lover, so I got it.

    • CH says:

      I’ve asked that question before on the other side of the table as the interviewer, and I’m always suspicious of people who answer, “This job, of course!” because seriously? I ask it because it gives me some insight into a person’s values and work ethic. Run a doggie day care, volunteer for a cause, study a language, learn to sing opera, write a novel – all amazing answers. Play video games, go on a permanent vacation, sleep – next candidate, please.

      • Victoria says:

        Seriously? What useful information could that question possibly give you. Do you actually care whether someone is more interested in learning Italian than playing Skyrim? In what sense would that make them a better employee?

        I’ve done a lot of hiring, and I really don’t think the gimmicky questions get you anywhere. Tell me how you’ve excelled and how you could apply those accomplishments here.

  13. Christy says:

    I once went on an interview where they asked me, “IF I were to walk into a room full of people who absolutely hated you, what would they be saying about you?”

    I answered to the same effect as I would answer a “What are your weaknesses” question but the interviewer probed for more info, wanting to know why people hated me. I walked out of the office feeling like absolute crap…later got offered the job, stupidly took it and was miserable!

  14. Megan says:

    My cousin was asked in a job for a retail position (while we were in high school) if she were going to steal from the store, would she steal $10 or a bottle of lotion worth $10. She answered that she wouldn’t steal, but they wouldn’t take that for an answer.

  15. JK says:

    I’ve been asked if I was married before. I am married so it was an easy answer, but it was still odd. I work in a mid-sized Southern city, so it was not super surprising.

  16. Staci says:

    I applied for the Technical Trainer job at my company. The first interview was filled with odd questions such as; If you were an animal what animal would you be? They must have liked my answers because I got a second interview. In the second interview I was handed a box and told I would have five minutes to prepare a five minute presentation based on the objects in the box: a ripped phone book, stress ball, rubix cube, calculator, and thumb drive. My presentation was on collecting information. It was really short of the five minutes though. I did not get the job.

  17. Rosanne says:

    During a interview for a office summer temp position, I was asked if some of people doing dirty, manual labor jobs made me uncomfortable. I was so completely shocked by this question – for reference, my father (whom is awesome and I love very much) is a carpenter and I grew up helping him in his workshop – and how out of left field it was. I truthfully told them no, I was not and am no stranger to saw dust because of the family business – and then followed the question up with why is that relevant to a job at a bank call center? She said that the receiptionist had thought I looked uncomfortable while waiting and there were laborers in the waiting room of the agency. My original interview had been rescheduled, but only AFTER I had trucked my way through 90+ minutes of traffic to get there on time, then waiting ANOTHER 45 minutes for someone to tell me my interviewer had called in sick and her replacement wasn’t available. I was noticibly annoyed they hadn’t called me earlier – my appt was early-afternoon, presumably they knew she was out sick first thing yet hadn’t bothered to either notify me before the appointment or when I first walked in the door. I replied that it was probably showing on my face how I felt after that experience and had nothing to do with other temps but the company that would handle prospects that way. She followed that question up with “how would I make a peanut butter and jelly sandwich?” I happen to be allergic to peanuts so I wouldn’t ever make one so I let her know that I wouldn’t be able to because I’m allergic. I suppose my answer was too literal, but seriously? A freaking sandwich? What brilliant HR book did they pull that one out of?! Yeah, I didn’t get the job, didn’t get a call back, didn’t get anything else from them and I’m better for it.

  18. Jenny says:

    I was once asked what my parents did for a living. I found that totally out of left field and somewhat inappropriate.

  19. I once ended up helping an interviewer buy an anniversary present for his wife during an on campus screening interview. It was odd, but there were so many of them that at the time it just seemed like part of the blur.

  20. Melanie A. says:

    I was once asked if I was pregnant during an interview and I was so surprised I half-shouted “No!” (I wasn’t, I’d just returned from my maternity leave from a job in a different department for the same company). I was so surprised because it’s illegal to ask that in a job interview in my country.
    And I’ve also been asked (while interviewing for a day care teacher position) to have a try fixing a broken oven during my job interview (which started 45 min late due to the appliance repair person being late).

  21. Melanie A. says:

    Sadly I couldn’t fix the oven but I did get the job and worked there happily for 3 years.

  22. Emily says:

    I was once asked by a very conservative congressman’s office which church I attended regularly. I wasn’t offended but it definitely is not something that applied to the job. I wasn’t offered the job.

  23. Lisa says:

    I have been told what nasty things I would be doing with the manager in the office and how would I like it…
    That I would not be getting the job because I don’t have kids and they want a single mom who want to be home so they can close the office early most days of the week…
    And my personal favorite: can you pass a drug test? Only to be lectured by the interviewer about how he was absolutely sure than I could never pass it.
    Oh yes, and many, many times I have been asked by interviewers (mostly men, but some women) how many boyfriends do I have. (In case you are wondering, I am decidedly NOT hot and dress very conservatively. I have been told I look “exotic” whatever the F that means.)

  24. Anyone says:

    I’ve got two:

    1) It was my first interview out of college (a somewhat elitist college that I had worked super hard to get into and pay for). THIS was IT though!! I was a perfect fit; I would be great at this job. I was so excited but completely insecure about my interviewing skills. I had gotten up very early (2am) in the middle of winter to get there b/c I couldnt afford a hotel room at the time. I was super nervous, tired and the interview just went so-so. At the end, I was exhausted but trying very hard. The interviewer helped me into my coat. Inside the coat, the dry cleaning tag was still attached to the label. The interviewer with a straight face but a cold edge to his voice asked if “I thought I was better than everyone else because I had my clothes dry cleaned”. I was so taken aback especially since I was NOT one of the trust fund kids at school and was barely making ends meet. Getting my coat cleaned (and a new suit etc) for the interview had been a real reach for me financially. I was so flustered, I mumbled something like “no, and only the coat ever gets that kind of treatment anyway”. It sucked as an answer and I knew it. I knew I didnt get the job as the interview got near the end but that question felt like a mean kick-your-ass-to-the-curb to solidify just how much I didn’t belong at that firm, at that interview, in the big city, out of college. I felt the wind blow completely out of my sails. 20 years later I still can feel the bitter disappointment of that failed interview and the anger at the bias of the interviewer for assuming I was someone I wasn’t. ….and I still think I would have been excellent in that job.

    2) A few interviews later, my mother in law had died a few months earlier of lung cancer and I was wearing her coat. Inside the pocket she had left a lighter, which for some inexplicable reason I had continued to keep with me even though I’ve never smoked a day in my life. I walked into the interviewer’s office. He saw me walk in then opened up a newspaper, put his feet on the desk and said “Impress me.” A red mist rage filled my head. I did the first thing that came to mind. I grabbed the lighter, lit the newspaper on fire and stomped out of the room. Didn’t get that job either. At least I had learned from my first fiasco and this time, I made an impression (the look on his face was priceless). (who would want to work for such a place?!)

  25. Amanda says:

    I have a couple…

    1. Name 10 things you can do with a pencil. (I understand it was a critical thinking/personality question, but still took me by surprise.)
    2. Are you the type of woman who can be friends with other women? (Ended up being a nice guy/boss, just a little socially awkward at first.)

  26. WR says:

    At an advertising agency interview, the first question out of the interviewer’s mouth was, “Are you an asshole?” Nice. I get it; he thought he was being clever…He explained that ad agencies are notorious for their high-maintenance designers and writers, and this was his way of addressing that up front. What do you say to that without sounding either defensive or…like an asshole? I just laughed and said, “I know what you’re trying to ask,” but it was such a red flag and the guy’s demeanor was so off-putting that I knew the job was not for me. A friend who worked there ended up quitting and later told me she was glad I never had to work for him. Bullet: dodged.

  27. National_Anthem says:

    In an interview for an associate position at a law firm, I was asked in quick succession if I smoked and if I owned a gun, and it was asked in such a way that implied some connection between the two questions. I was caught off guard, answered honestly (no to both), and then we sat in silence for about a minute. It was weird.

  28. melissa says:

    belle, i would totally read a blog post about your pageant days. one of my good friends did just a couple of them, and i still don’t really get the whole culture of them.

    also, i’ve gotten the “what dog would you be” question before. it’s awkward, but it was to work at a pizza place in high school and i got the job. apparently “mutt” was a good answer.

  29. Philly Girl says:

    I was once asked,”where did you grow up?” Which I thought was a fairly innocuous question. I answered, “the suburbs of Philadelphia, why do you ask?”. The interviewer said, “oh (with a judgemental scowl on her face), you have a strong East Coast accent.” I tried to make light of the comment and said, “yes, I guess you can tell I grew up back East, is that a problem?” She replied, “your accent makes you sound uneducated.” I asked where the interviewer was from and she said, “the mid West, and my lack of an accent demonstrates my high education level.”. I made a smart -ss comment of, ” at least I don’t sound like Rocky Balboa from the movie ‘Rocky’ and I guess this interview is over.” I got up, shook the interviewers hand and walked out. I cried all the way home. That was 15 years ago and it still pains me to think about the situation. Truly one of those moments in life that could use a ” do over”,

  30. Maharani says:

    I once was given a request at a round table interview at a biotech, “Give a seminar”. I did and was told it was quite good.

  31. ET says:

    My senior year of high school, I went on college tours with my parents throughout the East Coast. We decided to add an extra school to our trip along the way (a particularly prestigious small liberal arts school), and stopped by the admissions office to get information on tours once we arrived in town. It was the end of the day and we were there for 2 days, so we expected to come back the next day for our campus visit. While in the office, they informed us that an interview spot had just opened due to a cancellation, so they could interview me right then and there (there were no available spots the next day). They highly recommended an interview, saying that due to the high number of applicants it would be a great advantage. I was comfortable with interviews at this point and pretty confident, so I agreed. My interviewer was a senior at the school, and I felt that she immediately had an attitude towards me once I walked in the room. I thought the interview was going fairly well despite her attitude until she asked me after I explained my some of my service involvement, “So do you feel awkward helping poor people while coming from such a privileged background?” I was shocked and offended. I had never said anything alluding to a “privileged background” and since I was a walk-in, she had no previous information about me or any basis for her comments, other than the clothes I was wearing. After 20 seconds of silence and fumbling that felt like an eternity, I responded that I didn’t feel awkward about helping others, but just felt fortunate to be able to use the privilege of my great education for the benefit of many. 4 months after the interview, it was the only school I got rejected from.

  32. Rebecca says:

    At a company-based interview for a temp assignment, one of the interviewers straight out asked “Are you single?” I was quite taken aback, and, having just completed a semester studying Industrial/Organisational Psychology, my reaction was to laugh and blurt out “I don’t see how that’s job relevant!?”. This was coming from the female interviewer and not a flirtation – she then went further to ask if I was married or not, because their past hire had children and was always taking time off to look after them. Clear discrimination! Even if I was married it wouldn’t mean I had kids! And if I did, that shouldn’t effect my chances either. Despite this I was offered the role and took it at the time, but when I was offered a better one a few hours later I was quite pleased to be able to decline the first offer! NZ employment law is not that different from the US but clearly not all employers understand it.

  33. KH says:


    I have found this blog post particularly insightful. Wow, who knew all the crazy, random questions people have gotten thrown at them.

    Belle, this post is one of the reasons I enjoy reading your blog – career advice (with, of course, a dash of fashion). Keep ’em coming!

  34. Linnea says:

    Summer after my freshman year of college I applied to work at a children’s portrait studio. During the interview the woman interviewing me climbed up onto the little bay in the studio, sat cross legged and said, “Pretend I’m two years old and make me smile.” It was so uncomfortably funny for me. I think I went for the “I’m gonna get you!” and coming forward like I was going to tickle her…

    I did work there that summer and it was a (mostly) fun job, but that lady really was a little nuts.

  35. Heather says:

    While in college, I skipped a final exam and took a 10 hr train ride to DC to interview for a post-grad staff assistant job with a Congressman’s office who gave me 1 day’s notice and only one option for an interview time, only to be asked one interview question- “What’s your favorite band?” Did not get the job.

    Then, my last job, the man interviewing me made me come for an interview at 6:30am (even though the office didn’t open till 9), obviously, it was just the two of us there and he only asked me questions like “What do you like to do for fun?” “What do you like to wear to work?” “Do you work out?” Obviously this was extremely sketchy, and not appropriate for the government job I was applying for, and I got a bad feeling from it. But desperate for a job, I took it, and the man spent the next two years sexually harassing me. Belle’s first instinct tip is spot on.

  36. Emcie Kaye says:

    I love reading these comments! Wow, so many crazy interviews!

    I work for a large local government that has made providing excellent customer service a top priority. As public employees, our “customer” includes every person with whom we interact: residents, co-workers, the media, etc.

    I recently interviewed several candidates for two positions relating to social media/communications. I asked them to share an experience of a time they provided excellent customer service. Most of the candidates seemed very taken aback by this question and reverted to a story about their high school retail or restaurant days, not connecting “customer service” with government or their more recent, post-high school jobs.

  37. Capitol Hill SE says:

    I had an interviewer hand me a piece of paper and ask me to design a trashcan. I don’t think I came up with anything revolutionary so I didn’t get hired.

Join The List

Stay up to date on the latest from Capitol Hill Style!


Ask the Editor: May 2024 AMA

Every month, I solicit questions from my Instagram followers for an Ask Me Anything. So let’s get to some fashion questions.



Recent Posts

Ask the Editor: Root Touch Up Tips

As we age, we deal with the changes in different ways. Maybe we accept them and move on. Maybe we try to lessen or conceal them. Maybe we fight back like a UFC fighter. That’s why there are many ways to deal with graying hair.



Ask the Editor: Swimwear for Your 40s

The unofficial start of summer means that pools across the country are opening and beach trips are on the horizon, and that means swimwear. And the older you get, the tougher it can be to find the right suit.




Ask the Edit, Style, Top Posts | May 29, 2024

Ask the Editor: May 2024 AMA

Every month, I solicit questions from my Instagram followers for an Ask Me Anything. So let’s get to some fashion questions.



Ask the Edit, Posts, Style | May 29, 2024

Ask the Editor: Root Touch Up Tips

As we age, we deal with the changes in different ways. Maybe we accept them and move on. Maybe we try to lessen or conceal them. Maybe we fight back like a UFC fighter. That’s why there are many ways to deal with graying hair.



Ask the Edit, Posts, Style | May 28, 2024

Ask the Editor: Swimwear for Your 40s

The unofficial start of summer means that pools across the country are opening and beach trips are on the horizon, and that means swimwear. And the older you get, the tougher it can be to find the right suit.



Ask the Edit, Posts, Style | May 23, 2024

Ask the Editor: Vol. IV, No. Twenty-One

This week, the reader mail bag was full of little things. Pajama advice. Jewelry cleaning tips. Small things, but ones you might also be curious about, so let’s get started.