I read the post by CharmingRougue about boring girls that don't do anything. I had the exact same problem this past weekend. This pretty girls was giving me an IOI(eye contact and smiling more than once) I opened her and started a conversation, the conversation went something like this:

ME: "What are you doing with your life?"

HER: "I don't know. I'm taking a break from school, I was three years in but I don't know what I want to do, so I didn't want to waste all that money in I don't know what I want to do."

ME: "I guess that leaves you a lot of time to work and make some money, do you have a job?"

HER: "No, I'm going to look into being a waitress."

This is where I got stuck, she wasn't in school, she didn't have a job, it seemed like she wasn't doing anything with her life, I didn't know where to go next. I'm sure CharmingRougue felt the same way, does anybody have any suggestions?

Listen to what she says and ask about what she told you.
You could have inquired about why shes taking a break?