Jill sounds like a fun person! I'm very interested to see where this goes =). It's been a long time since I was in high school (freshman year 1993, anyone?), so this is fun to get back to the antics of high school =).
All of your stuff is good. Is "Blackend Sight" coming along any time soon?
Good start here. It will be interesting to see what happens. I could see her just gauging a reaction (I've asked my SO such questions before), or she could be serious. I'm interested to see more.