Talking to people, the single most frequent first response is “I don’t get it”. Then we take the time to explain it and then they are like “Oh, I see. That’s cool”.
You said you failed to connect with people on an emotional level, but I would contend that you failed to solve a problem perceived by the customer.
Only when you solve a customer's problem will you get that emotional connection. It's not something you need to work at, it's something you either succeed at doing, or fail. I would say that your application just didn't solve anything someone was looking for.
Your questions led you down the wrong path. Your very first questions should have been:
1) What is the pain point that X have? 2) How can I solve that with an iPhone app?
Where X is anybody you thought you were solving a problem for.