There have been successful relationships though, right?
I'm a regular Christian married to a Witness. We still have many conflicts over religion, but we make it work with lots of communication and compromise. Neither of our congregations are happy with the consequences of our union. Both carry a faint hope either one or the other will convert to them. I would not have married him if we intended to have any children, however. I would not impose this sort of crazy marriage on an innocent.
You're right at the beginning, thinking of dating, right? What is the risk? She will say no. Oh well.
What if she says yes? You got a whole can of worms to deal with. Are you willing, for instance, to imagine her and your newborn child dying during delivery from loss of blood, and letting her do it because of her beliefs?
I would say other than "athiest", you are the least prepared to deal with the complexities and the commitments being a Witness or a friend of a Witness. You are a nominal Christian. You don't know why you believe what you believe. You haven't researched the foundations of the Orthodox Christian point of view. You can't spot the inconsistencies and the illogic in the Witness beliefs. So besides being unprepared for the emotional toll of your differing beliefs, you are ill-prepared to discuss the foundations of your respective beliefs.