I did talk with a theology student who had the opinion that everyone is going to heaven because Jesus did on the cross for human's sins. Before asking more specific questions about heaven and hell it's useful to to know the stance of the person you are talking to.

Afterwards you can force them to be more specific and name hard numbers. Pressing a believer into giving you hard numbers can switch them of reciting established talking points.

"Yeah, it seems stupid and nonsensical, but I believe in God and I believe that this is what God told me, so I have to have faith that it makes sense."

In that case I would check how they know what God told them. God directly speaking to them? Them reading the bible? Don't different people interpret the bible differently?