Twenty Twenty: 20 Twentysomeones On The Hardest Interview Question They’ve Ever Been Asked!

Over the past month I’ve been asked what seems like a million interview questions. I’ve had some fun ones. Robin, what do you do on the weekends? Umm party? Where do you like to eat? Chipotle. Too basic? What’s your favorite drink? Is this a trick? I’ve had strange ones. Do you think you could be famous? Ummm could, should and waiting. Tell me a joke. Want to hear a pizza joke? Nah too cheesy. And then I’ve had some tough questions. Tell me about a time you had to build a strong, lasting relationship with someone who was nothing like you. Do exes count? Tell me about my company. Well, let’s see here. Tell me what was on the front page of the paper today. You do read the paper right? Why of course! Think. Think. Think. Why are you so special? Because my mommy said so! Those were, of course, my immediate reactions that I kept to myself. I asked twenty amazing twentysomeones to tell me the hardest interview question they’ve ever been asked. Their answers are below.

Fill in the blank. At my worst I am _________. At my best I am _________. -Ashley Gaymon

What qualities would make someone a better candidate for this job than yourself? –Jovan Julien

What did you tell your current employer about where you were today? It was either a trap or they were looking for their own personal excuses the next time they had an interview.-Alyssa Ruiz

How would you live your life differently?-Justin Harlow

I was interviewing at a Chicago ad agency and we were on the subject of social media. I brought up Twitter and how useful I thought it was, and the interviewer asked to see my twitter feed. Of course I had to show him, but while I was happily pulling it up, I had a mini panic attack trying to remember if I had tweeted anything ridiculous in the past few days. Not a good feeling. It wasn’t so much a hard interview question but I learned a lot from that situation. If you’re on the job hunt, be ready to explain anything that you put on social media sites! –Carmelle Kendall

How many manholes are in NYC?–Justin Weiss

What is your biggest fear?-Margaret Parham Holt

Don’t post my pic. And I need a pseudonym. Preferably Quiktripshawty. The hardest interview question I was ever asked is “Where do I see myself in 5 years?” Like let’s be serious, I don’t even know what I’m going to do in 6 months. Hopefully I’ll be in Atlanta, but I’m realistic, I’ll probably move back right after the Hawks win the NBA championship.-Quiktripshawty

Mine was dental related so not sure if it will help! It was during one of my residency program interviews.What would you do if they invented a vaccine against caries (tooth decay)?-Jocelyn Robelli

What do you think makes a great school? If you’re in education or have worked in schools, you know this is a loaded question. So much goes into making a great school, distilling it to a few talking points was a challenge. –Adeel Khan

How many planes are flying over the US at this very moment? I couldn’t google it as I was interviewing for them! They weren’t looking for a right answer, just my thought process.-Sherry Almasi

What went wrong? A reporter asked me that after taking second in the 400 meter hurdles at the 2005 High School National Championships. I was the favorite to win, but lost despite running a personal best time.-Justin Gaymon

Besides case interview questions, which are a totally different animal–I think the hardest interview question I’ve ever been asked was, what is one way you think this role may not be a good fit?-Bhavna Batra

It’s a tie. These two questions weren’t “hard” but they were tricky so: how would you sell ice cream to Eskimos? Also, how many tennis balls will fit in this room?–Nicholas Hamlett

Before we conclude the interview, what else should I know about you?-Jessica Tuan

Tell me about yourself. I’m pretty sure they ask that in every interview, but what does the interviewer really want to know?! It’s too broad for me to know how to answer. In my last interview I panicked and said I played rec. sports. I thought I completely blew it, but I later found out that my boss played soccer in college and I think that’s why I got the job.-Lauren Doroghazi