How to have a meaningful date conversation – See this now!

5. Ask them how they feel.

Don’t be shy about asking your date about the feelings that led up to important decisions in their life. A subtle but effective approach is by asking “why” questions: “Why did you choose teaching as a career?” “Why did you move to New York?”

Listen for whether the answers are concrete or emotional. “Teaching gives me summers off” might indicate concreteness while “I love children” discloses a strong emotional core.