Discreet questions to find out about someone

There are several situations where you might want to know something but asking outright is dangerously close to being rude, and might even be offensive. One of the classical situations is a job interview, where as a candidate you don't want to be seen as too forward, but you want to have the information.

Some questions in such a situation could be:

• "What happened to the last person who did this job?" - the answer to which could give you an example of how they treat people (he was laid off, he took leave, she gave birth, etc). 

• 
  "Why isn't the company promoting from within?" Listen for the corporate philosophy as well as the boss's reasons. It will give you insight into potential snags in your own upward mobility. If many people are being brought in from the outside, find out why.

• 
  "Who will evaluate my performance?" When? How? This question could be the most important one. For example, if your evaluator won't be working closely with you, you'll need to know how judgments will be made.

I can't give you examples for questions, but I can tell you that whenever a guy comes over and starts babbling about where he'd seen me before and if I have a brother I want to throw my drink in his face.

I mean, come on... at least come up with something original... (Oh, and FYI, it's much much better to ask me directly if I'm interested. It's way less offensive than boring me half to death). 

Might I suggest, if you see a heavy set woman, do not (under any circumstances) ask her if she's pregnant, even if you're dying to know, your father is the leading gynecologist in the land, and you want to give her a reward for being pregnant :-)

I can't think of any woman who wants to be considered pregnant if she isn't... 

It very much depends on the situation and what kind of intimate detail you are trying to figure out. Is it a job interview? wanting to have sex with them? trying to get a friend better? trying to get to know a possible partner better?

However there are some things that can tell you a lot about a person if they choose to share information. 

1) What's your biggest fear?

2) what is your first childhood memory?

3) what do you want to be when you grow up? (basically a cooler way of asking what's their dream job) 

4) what are your favorite movies \ books  \ music albums \ artist?

5) what's your relationship with your parents like?

6) have you ever had your heart broken?

7) what was the most scary things that ever happened to you?

8) have you ever been in a long term relationship? if it end then why?

9) what's the most crazy \ wild thing to ever did?

10) what was your first sexual experience like? 

do you love sex, would you make love to a sexy 70 year old man who is very sexy and loves sex?

Are you asking a man or a woman as it will make a difference