Terry, I too, communicated with an old JW friend in the past year. I really thought that after nearly 50 years (!) surely some lighbulb had gone on. Her hubby was an educated non-JW and she had 4 children and they enjoyed a privileged lifestyle. She enjoyed material advantages but I thought surely the odds favored some change in her circumstances and therefore enlightenment on her part.
A very nice e-mail from her disabused me of my wishful thinking - she and her hubby and children (save one) and grandchildren are dedicated witlesses. I haven't had the heart to answer her and it has been 6-8 months now.
It makes me kind of sick.