Asking open-ended questions—who, what, when, where—can be an effective social tool, but it’s often overused.
Asking too many questions in succession turns the date into an interview, and this often makes people uneasy.
Always be sure you add your own experiences, thoughts, and opinions into the conversation and show who you are.
When someone is giving an answer, be certain to BE PRESENT, rather than plotting in your head on how to keep the conversation going.
Wait, you mean I shouldn't have been asking about salary ranges and for a letter of recommendation?
Use active listening, ask questions about their responses, and try to understand what their viewpoint is.
Most people tell you who they are, if you listen to them long enough.
If you want to learn something specific instead of asking them a direct question, give them a fun story from your life that's around the topic. And let them organically contribute. It feels less forced, and you get to see what they think is important
As cliche as it sounds, just be yourself. Have a conversation like you would with anyone you're not on a date with. If it flows organically, it's a good fit for continued dates. If it feels uncomfortable, it's not.