Well I never interviewd someone, but maybe thinking and planning interviews upfront is a good idea. As a pro you are likely to do that already, but maybe go a bit deeper then just lining up the questions.
Judge the persone your gonna interview and base the questions on that persone. If its a persone thats pretty much a jabber (someone who talks your head off), then asking the right question can get you all the info you want.
Also building a small 'friendship' infront and during the interview may give you better acces to more dared questions.
In other cases you just have to dare, or ask the question propperly. Maybe call a bluff.
For instance if you want to find out if someone has had sex with someone (in the trend of 'scary questions), you could ask: Did you have sex with that persone. Or call a bluff instead and say: So, we heard you had a small... intens... relation with that persone...
Then see if the persone finnishes it off. Maybe she doesnt know what the hell your talking about and she will just tell you.
I think questions like this are just a risc no matter how you ask them. It depends on how open the persone is, and how big there sence of humor is.
Hope this helped, good luck with it
