What is the most awkward question you've ever been asked?

Question

What is the most awkward question you've ever been asked?

Answer 1

"Are you sleeping?"  I don't know why she expected a yes answer.

Answer 2

"are you a virgin"

By a girl I had JUST met.

Creeeepy.

Answer 3

if i was a virgin

Answer 4

probably, 'whats your bra size?'

a guy asked me that.

and its embarrassing because i have small b***s.

haha.

talk about awkward.

Answer 5

"have you ever masturbated, haley? like, do you ever get a... a sensation?"

my mom

Answer 6

I got asked this in two job interview... "Describe a time when someone disagreed with what you were doing and how you handled it"... what the h**l am I going to say, " I beat their a s s".  I just think that's a dumb question and I never answer it like they want me to.

Answer 7

From a 3rd grade student where I teach: "If I do a good job on this test, can I massage your feet?"

Answer 8

what are you doing? my guy friend asked right after i got out of the shower.  

Answer 9

LOL just stuff like:

when was your last period?

and

are you a virgin, how far have you ever gone with a guy?

and

how do girls m********e?

just silly and weird stuff like that. haha

Answer 10

When I handed in my passport application and got interviewed, I was asked how it was that I didn't know the whereabouts of my mother.  I responded with a very sincere, yet sarcastic comment that everyone didn't have a loving mother.

Answer 11

"Are you married?" from a very rotund man 20 years my senior,eeesh!

Answer 12

if i was wearing designer braces (as in braces that go on the teeth). it was weird!

Answer 13

"What do you do for fun?"

Sure, it doesn't sound awkward, but it's the worst when you're a loser.