(If I could fit this in 2 minutes and if it applied to the person)
1. I like you anyway whatever you decide because my admiration for you as a person goes beyond whatever you believe or practice religiously.
2. I know you are a person who cares about the truth. And if you want to prove whether JWs have the truth or not you will do that yourself, and you don't need me to do it for you.
3. Experts in relevant fields have considered and rejected JW claims on chronology, evolution and whatever else. There's lots of specific information available from real experts on these subjects. Watchtower literature distorts and misunderstands a lot of these issues.
4. More people are leaving JWs now than ever before and JWs are beginning to decline in many countries. There is lots of support from other people leaving or who have left already, if you need it, online and locally, probably including people you have known as JWs in the past. You might be surprised how many people you know who have already left or want to leave.
5. When people eventually leave JWs a very common thing they say is they wish they left when they were younger and didn't waste so much time in the religion. As 1914 recedes further into history, and the "generation" gets stretched out even more, the GB are only going to get crazier and more demanding as time goes on.