While getting a third party may help ameliorate the generation/experiential gap, it may not always guarantee it.
People’s experience even within generations may be quite variable. For instance, someone who didn’t take part in the '60s countercultural/anti-war protests in the boomer generation may not always be able to relate to those who had. Got to see plenty of infighting not only among boomers, but even among Vietnam vets over those very issues while growing up in a former working-class NYC neighborhood in the '80s and early-mid '90s.
From observing them, it was almost as if they were from different societies/generations despite them being from the same society, same generation, and presumably speaking the same American English.