I think progressives never thought about this because we banked on immigration and demographic change allowing us to win culturally and electorally but the issue is immigrants tend to be overwhelmingly male, that is how Trump won actually he won over a lot of Hispanic,Black,Asian and indigenous men who feel humiliated by a new culture, economy and world.
So what can we do rhetorically and policy wise to win more young men over ?
Do what you say you’re going to do when you get elected. Quit finding just enough no votes and making excuses. You promise, we vote, you don’t deliver. Then you ask “why does no one want to vote for us? We promised to be marginally less terrible than our opponents!”