nateb - I always comment on how tired and exhausted they look. This prompts them to vent about the rigorous JW schedule. Then I ask if they're happy. Invariably they say yes. Then I say that's great and that's all that matters. Then I say just so you're not expecting the end to come in your lifetime and you're planning for a good long life you're on the right track. Then I wish them well and remind them that I'm available to them.
Hi roxanesophia, I agree with other posters who have said to avoid talking about doctrine with JWs. I like what nateb suggested because you might be able to reach a JW if you can get them to examine how they feel and that you are always available for them when they are feeling down. I would suggest that you have at least two different types of questions. One type of question(s) for when you meet a JW without a biblestudy and one for when a JW has a bible study. When a JW does not have a bible study, you could ask "Why are you still a JW?", if they give you the typical WTBTS' lines then say "Really, is that how you feel; I asked you about your personal feelings.", and then end the conversation with "I am always available for you when you want to talk about how you really feel." The other type of question(s) for when you meet a JW with a biblestudy, might be like what nateb wrote. When you talk with a JW with a bible study, you want to plant seeds of doubt in the bible study. Good-luck with planting roxanesophia!!
Peace be with you and everyone, who you love,
ABibleStudent