For me, I could see very early on that any debate with a JW that uses the Bible or their literature usually fails. I find that talking about " personal feelings" works best.( were you upset about 1975? did you skip college to pioneer- do you ever wish for the career you missed out on to pioneer in 1975?, etc) If I can get them to admit to being unhappy about anything in the Org., it's a start. As long as they deny being unhappy, then why bother? I agree with Gary- be happy, live happy, be successful and make new friends. Someday the arrogant self serving JW leadership will finally make a mistake and get thrown to the dogs.
shalom,
Moshe