How to transition from friendship to dating?

A male friend and I have been doing this slow dance of courtship (flirtation?) for over a year. I'm falling for him, but I have not let my feelings known. Signals from him have been... steady-ish (I guess? Perhaps not really). I don't think he's the kind of guy who pursues women, ever.

This ambiguity and lack of development are maddening. I'd obviously like to date him, but at the same time also don't want to push it too hard and risk a rejection. What's the best way to proceed in such delicate situations?
How to transition from friendship to dating?
Post Opinion