Ok Ive been out of the game for a while, but I know some of my sticking points.

1) My main trouble is when I do approach I cant seem to generate anything more exiting than the interview method. "What you studying", "why you like that", etc.
So how do I break out of this sterile boring conversation? Its really bugging me!
My life stories are pretty ordinary and when I do try to spice something up it comes across as lame and boring.

Because all I am doing is asking questions I run out of things to say.......awkward pause......wait a little longer, just in case.......eject


Example:

ME: "Hey how you know john?"
HB: "Uni"
ME: "Cool, what you studying I havnt seen you around"
HB: "Art"
ME: "Thats a pretty broad topic, what exactly in particular?"
HB: "History"
ME: "Really, what type local, roman, greek?
HB: "Just general stuff"
ME: "My friend Kat she got to go over to Sicily for the second year field trip last year"
HB: " Yeah, I do that next year"
ME: "....."
HB: "....."
ME: "bye"
HB: "cya"

try making assumptions. Instead of what are you studying, try you look like an art major. This will make her more involved in the conversation

Don't be afraid to talk about stuff YOU'RE interested in. As long as it's not something too weird, you should be able to get her interested with your own enthusiasm.