Embarrassing Things I’ve Done When Looking for Work 

You’re looking for a new job. It can be either your dream job, or your just-for-now job, but the process is still the same. You update your resume. You send emails. You have phone interviews where you hope the interviewer can’t tell by the sound of your voice that you’re not wearing pants. I’ve been there and have made mistakes so that you don’t have to.

Informational Interviews

A friend put me in touch with his friend who was in the industry I was hoping to break into. After some emailing, he graciously agreed to meet up for a drink, so I could pick his brain. I wrote down a list of questions I wanted to ask, and was excited to hear the advice he would give me. I was trying to keep my expectations in check when I arrive at the bar and realized there was a slight problem.

Now it may have been the lighting of the bar, or the tweediness of his jacket, but he’s definitely within the range of dudes I would be attracted to. Oh no. I keep asking him questions, but while he’s answering all I’m thinking is “I wonder what my listening face looks like right now? Stop! Listen to what he’s saying. Although what if this is our meet-cute, but then our dynamic is such that he tries to give me advice all the time? I think I would hate that. Or I might be into it in a Jack Donaghy sort of way? Ok, must focus. I wonder what my focused face is looking like right now?”


It was time to order a second drink. He ordered whiskey (they always do). It was my turn. I remember I was aiming to sound cool and laid back (with my mind on my money, and my money on my mind) when I heard myself say, “I’ll just have a gin and juice please.”

That didn’t work.

“Really? I’ve never even made that. What kind of juice do you want in that?” the bartender eyed me skeptically.

“I guess cranberry juice? Cranberry juice seems straight out of Compton, right?”

“I don’t know. Ok, cranberry juice and gin it is.”

“Great, thanks! Actually can I just sub out the gin for vodka then?”

Rookie mistake. Never try to be cool. Remember, you are your own worst enemy. Also, no ambiguity is best in these situations. Therefore I’d try to meet for these sort of things in neutral locations where no one has ever felt any sexual tension, i.e. coffee or a lunch where you both are eating difficult things like salads or burritos.

First Interview

These are usually a breeze. We’re going through my resume line by line, I’m explaining away my bachelor of fine arts as a youthful dalliance, much like experimenting with one’s sexuality or veganism, when what I really want to do is “whatever that company happens to do.” Everything’s going well, the 55-year-old recruiter is asking my availability for a second interview, when I see a photo on his desk of three women in their twenties. This is my in!

“Aw, you have three daughters? I’m the middle of three girls. They look really close.”

He looks at me the way I look at people when they tell me they don’t like dogs.

“No. I have two daughters. The one in the middle is my wife.” OH NOOOOO. We have a Soon-Yi situation on our hands. Must save this.

“Well, you know, your wife looks very youthful, so…congrats.”

Lesson: Don’t comment on people’s framed photos on their desk. Unless they’re in a photo with someone so high-profile, it would be weird if you didn’t comment on it. Like a former President. Or Andy Cohen.

Stock Answers

As everyone knows, it’s important to have certain stock answers at the ready, since they come up so often.

“What would you say your biggest weakness is?” should always be answered with “Excel.” No one actually expects anyone to know all the ins and outs of Excel, and I anticipate it will be phased out any day now. (Note: This is actually horrible advice. Excel will be used for the rest of Time, and will outlive us all. Also your subpar skills will make you beholden to the person in the office who is the best at it, Smug Excel Guy).

“What do you like to do for fun?” This seems like a no-brainer. Just display a smattering of varied interests that makes it seem like you are a well-rounded person, and unlikely to spend all of your free time on only one intense hobby. (Shout out to my friend who is obsessed with talking about how he brews his own beer.) Just quickly plan what you say in your head first.

How you should answer: “Going to the movies, seeing friends and family, and volunteering.”

How I answered once: “Going to the movies, comedy shows, reading books, and I like tapas bars.” 1) You know what sounds exactly like topless bars? Tapas bars. 2) Tapas bar? That’s right up there with “hip nightclub” as expressions I only use when I’m nervous or trying to explain my life to my grandparents.

“What are some of your favorite movies?” is the job interview equivalent of the “what kind of music do you like?” question in dating. There are no winners with this question, and make no mistake: You are being tested.

How you should answer:It’s a Wonderful Life.” Boring and safe. (And wonderful!)

How I answered once: “Oh wow. I guess the usual movies everyone likes… Let’s see, off the top of my head it would be Christmas Vacation, Annie Hall, umm City Slickers…and (at this point I realize I’ve completely lost the 65-year-old man interviewing me, and am trying to relate to him when I see golf clubs in the corner of his office)… and of course, one of my all-time favorites, The Legend of Bagger Vance?”

Spoiler alert: Naming period golf films that you’ve never seen will get you nowhere. I didn’t get the job. On the plus side, I did reignite my interest in City Slickers, which I would have forgotten about if it wasn’t for my stream-of-consciousness job interview.

Lessons learned: Be yourself, but try to be the most put-together version of yourself. If you do happen to say anything embarrassing, just write it all down and eventually put it on the internet and hope that no future employers see it.


Michelle Markowitz is a comedy writer and storyteller in New York.  She co-hosts the comedic storytelling shows “Failing Our Twenties” and “Hookups & Hang-Ups,” and can be found online (usually talking about her love of Chipotle), and receives links to animals doing cute things at her email address.


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