IMO, here's where you're going wrong just with the example you gave.
Quote:
Me: "So how's your shopping going?"
You gave her a great compliment that probably piqued her interest in you. The problem is the question you're asking is basically going to allow her to give an automated response, in essence, that immediately causes her to lose that interest. I would have guessed that she would say something like "fine" or "good" the moment I asked.
I'm not saying that it's not a good question, but it should have been asked in a different way or followed up with a question that would allow her to expand on the answer:
You: How's your shopping going?
Her: Good.
You: Don't tell me you are one of those women that loves to shop...
Going that route, you'll start moving the conversation to an emotional level and getting emotional responses. That's your opportunity to agree and/or understand her (in her eyes) which will lay the foundation of building a rapport with her.