Sherry - he seems AWFULLY interested in what you were wearing and whether you had a good time!
Don't worry about the "you should go out with..." comments - many WASs say this stuff, then FREAK OUT when they think the LBS might be taking them up on it. In fact, several former WASs on this board have said they told their LBSs to date, thought they meant it, then panicked when their LBSs took them up on it.
I suggest you dress up real sexy and go "out" for the evening with "friends" - even if all you do is sit and read at Borders with a cup of coffee Let him start to wonder what you are up to.