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 ?
It’s quite possible it’s the other way around on that one. I’ve certainly had periods of my life where I had to branch out pretty far in my social circle to meet women because the things I enjoyed doing are either solo activities or of little interest to women (at least around here). Some of that has gotten better in the last decade or so as nerdy shit has become more socially acceptable and ive built up a more diverse social network for myself but it was a rocky start and if I didn’t get lucky with the people I had around me it could have turned out much worse.