While I understand and have used the 'ask questions' theory I have also found that jw's just seem to get a false hope that one day, like us, they might say the right thing and low and behold you will see the light!
Ask questions yes, but know your jw doctrine and know your Bible (not a NWT, though you may want to look at the KIT seeing as no jw ever does).
edited to add- I wish all the best and hope he really does see the light soon! carla, another ubm