Here's an example of what we're on about.

I went in a shop the other day to buy some cigarette papers. The guy at the desk looked totally bored and there were no other customers so I started a conversation with him. We talked for about 15 minutes about all random stuff and I think it cheered him up a lot. I enjoyed it too.

To progress I need to be able to do this with a hot girl. But you can practice this almost anywhere, anytime as well as approaching attractive girls. It sounds like doing this would help you along.