Disassociate yourself from JWs, and join the Loyal Order of Water Buffalo. They've got a bowling team.
But seriously, YES, trying to wake up a friend, even a close friend can be very risky if done directly. Like DesirousOfChange said, most JWs will go straight to the Elders. They aren't trained to handle any questions that don't follow the script of their publications, and they imagine that the Elders have some extra special experience to 'help' you. If you want to help others wake up while keeping yourself safe, use eyebrow raising information that can be obtained and verified from innocuous sources, especially JW publications themselves. And do so seemingly innocently, that's key!