What is the most awkward question you’ve ever been asked? – 19 of the worst examples

11.

“Hey man, mind if I squeeze in to try for her number?”

Dude wanting to hit on my wife whilst sitting together at the bar.
Spi2ee

12.

M4lkcontent
Via

13.

I was working in a call center doing tech support for a cable company. I fixed a lady’s cable and she was so happy she asked me if I wanted to marry her daughter. I politely declined.
TheRealOcsiban

14.

“Have you ever seen a dead body?” mid job interview.

I’m a mortician.
FarMortgage4127

15.

I was in a job interview and nervous and the manager asked me if I had a psychological disorder

I left.
Newtsheadwound

16.

“You look strong, can we wrestle?” – a man in the grocery store.
yokononope

17.

MadWifeUK
Via

18.

I was buying a pregnancy test at Walgreen’s and the clerk asked, “What do you hope the answer will be?”
Teknista

19.

Once at the grocery store a man chased me down to ask why I bought a certain brand of tortillas over another one.
kaitnurface

BONUS

“If you weren’t born around Christmas time, then why is your name Holly?” -a coworker angrily shouted this at me one year.
RimeFeatherMage
Via

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