I think for the time being, his not knowing you are behind the "letters" is a good idea, otherwise he will steer clear of you completely.
What about leaving a note with: "type in your search engine: watchtower research" ?
Why does the WT want very young children to baptize, being one of the most important decisions they'll ever make, yet says dating and marriage are only for the mature, older ones?
Why do Jehovah's Witnesses really take blood? If they are to pour the blood on the ground, how can they make the fractions used every day by JW's? And why can they use these fractions from stored blood, but can't donate blood for others use?
The Hebrew scriptures says "you are my witnesses" in Isaiah. The context is clearly speaking about the nation of Israel. Why do JW's take this verse out of context and apply it to themselves, when the Greek, NT, clearly tells us to be witnesses of Jesus in Acts 1:8?
A number of posters to this forum have given excellent questions to ask JW's. Here are the names and dates of posting. I think you can find them through the "member directory".
"Corvin" 25-Aug-04 entitled "Questions for Jehovah's Witnesses Regarding Doctrine"
"Lady Liberty" 13-Oct-06 entitled "Someone may benefit from this..regarding the Expos'es of the organization"
"Goldminer" 07-Sep-05 entitled "My list of 32 questions-Part B"
Hope some of this will help.
Peep