A good way to actually get to know someone and find out intimate things about them is to play a game or get a book that gives you interesting questions to ask each other. That way, you can really get to know someone without awkwardly trying to work this stuff into a conversation.
Ariely and his colleagues ran an experiment in which they gave dating subjects a list of 20 questions and instructed the subjects to only ask questions from that list. “Everybody benefited more from those questions,” said Ariely. The question-askers got answers that they cared about, and the question-answerers found the discussion much more interesting.
So next time you’re on a date, try asking something along the lines of “What’s your largest goal right now?” or “What were you like as a child?”