I think a lot of the problem is that the conversations are often disingenuous even when they start to happen at all.
For instance, when books with racist depictions (or depictions thought to be racist) are removed from schools, the Right screams about how important freedom of thought is. When books touted as anti-racist are removed from schools, the Left screams about how important freedom of thought is.
I don't buy it.
Neither side acts as though they care about freedom of thought. Rather, they act like they care about promoting their ideology, and "freedom" is a convenient cudgel to bludgeon the other side with.
When people on the Right push a highly simplified whitewashed (literally) America-the-Savior view of history, the Left screams about the importance of historical accuracy and completeness. When people on the Left push teaching the 1619 project, the Right screams about the importance of historical accuracy and completeness.
Well, isn't that lovely?
It's hard to make any progress on difficult societal discussions when the conversation rarely moves past hypocritical screaming.