I may have missed the point here so forgive me but I am curious as to what the original poster is trying to achieve. One may wish to question a JW to show them the error of their ways, or a friend or family member to help them to see the true situation. I am certainly no fan of WTS but if a person wishes to maintain their religious belief, why not let them if it is clear they do not want to have these beliefs challenged?
How close a friend is this person? It might be very difficult to develop a friendship with a truly committed JW. As a non-JW you will always be regarded as different and once she sees that you are not a good prospect for assimilation you may find it hard to have much in common.