23 Of The Most Ridiculous Questions People Have Been Asked In A Job Interview

Applying for jobs is one of the most annoying facets of life. And in a day and age where millennials are overqualified, underpaid, and fighting for entry level positions, it seems like employers are intentionally f*cking with us by asking some of the most ridiculous, crazy, and unprofessional questions in the book.

What douchebag bro thought it was okay to ask the woman being interviewed if she would “cry if her work were criticized” in an upper level engineering job? And who thought it was a good idea to ask about the interviewee’s relationship with their parents? Like, yes — my mommy issues have EVERYTHING to do with this middle management position at grocery store supply chain.

Last time I checked, interviews aren’t supposed to delve deep into a person’s strained relationship with their father or ask about their deepest, darkest political views, but apparently — interviewers don’t give AF anymore. And if I have one more wannabe Google-esque interview where they ask me how many pennies it would take to make a life-sized model of the Empire State building, I’m going to lose it.

These 21 interviews completely overstepped personal and professional boundaries:






Written by Laura McNairy

Laura is a freelance writer for TFLN. She likes to write about what she knows best — dating, sex, and being awkward, but usually in the opposite order. She is the Assistant Editor and videographer for Peach Fuzz, a sex-positive nudie magazine in ATX.