I'm with Outlaw on this one LouBelle.
If you're here looking for advice on what to discuss or how to handle him, you should not be talking to him at all. If you can't control the conversation, just don't let them start one in the first place.
He is not your friend.
He has nothing of value to offer you that you can't get elsewhere.
If you must talk to a JW, never let them choose the subject. Quickly turn he conversation to a subject you know they are familiar with, but that they will be uncomfortable with, and hammer them on that. Do not answer their questions, they are there to answer yours, tell them that. The more they want to trick you into a change from a particular subject, the more you need to stay on it. Don't express your own opinions, just use questions to make them do the talking and lead them to making conclusions that they didn't want to come to and to indulge in behaviours that they would condemn if a member of another church used them. Use guilt when they try any tricks, dishonesty, double standards, or bullying, and feign being offended that they would try to treat you like a fool etc..