"Why?" is a conversation stopper. Instead, use "Tell me more." That's a conversation starter. Both are prompts to try to get more information from the other person, but "tell me more" relays more interest in what they're saying. It can also come across as less judgmental. Acknowledge, ask. Acknowledge, ask.
Here's an example. Someone says they're going to Six Flags for the weekend and you respond with "why?" That implies that maybe you don't like Six Flags or it's a waste of time, or whatever the case may be. Instead, acknowledge and ask. "Oh, I haven't been there since I was a kid! What is your favorite ride?" See the difference?
