I think “So how was prison?” would be an inauspicious thing to ask.
“any recent herpes out breaks?”
In Florida, where most streets do not have curbs, we call them swales.
“How did you beat those rape charges?”
If you want to see a couple argue, ask them, “So, how did you two meet?”
A surprising amount of the time they will have differing memories of the event.
the verge…
I’ve sworn a blood oath to never again ask an Englishman to explain the game of cricket.
When I’m at a party and have troubles reaching “da ladies” because of my fellow geeks cramping my style, I ask…
Who would win?
Star-destroyer versus the Enterprise versus Borg cube versus…
Or sometimes I give then a simple math problem
Three pieces of wood, 1 of 1 meter, one of 2 meters and one of 3
The two largest pieces of wood are placed diagonal between two walls
And where the two pieces cross the third piece of wood is placed so it just reaches the ground. The 1 meter piece reaches up with a straight angle to the floor.
The question being, how far are the walls apart?
(The puzzle I write down on a napkin or what ever, not sure if explained is enough here)
Usually, by me.

Devilstrip!
Never, never, never if a woman starts to talk about her last pregnancy - do anything to indicate you give the smallest interest at all (Note: Assuming you’re a man).
It’s called… that strip of grass between the sidewalk and the street. Do we need a name for everything?
Also, I’ve had amusing results with “Have you ever really thought about where your dollar bills have been?”
I’m a woman and I hate birthing stories so much I’ve had to leave parties on several occasions.
If you had consulted your local DOT, you would have known it’s called a “beauty strip.”
Cite?
The area engineer at my local DOT.
Ok, make that Things NOT to say or ask in company when there are no Dopers in the group. 
The gentle sea cow … smokers?!
Oh, that’s manatee
No matter how big she looks never ask a woman when she is due.
I’ve actually done this. To someone who’s actually quite skinny. She was just wearing a loose summer dress that billowed outward a bit.
:smack:
See? SEE??? You can’t even raise the topic in here without people getting distracted by it…lol.