The only constant is change. I have put some thought into where I see things heading but I'm still trying to work through my own vision of the future of the mating environment. I've seen some good nuggets in existing posts I'll quote and respond to them. There are going to be changes in both the overall environment and the methods used to initial seduce (daygame, nightgame, etc).
I'm going to start first by going over methods and where I see those methods.
Online dating has some sort of future. Online dating websites and apps will probably fade to a degree but not completely go away between now and 2035. Gen Z saw what a disaster swipe apps were for Millennials during the 2010s and they haven't been inclined to use them as much. A lot of Millennials have had poor experiences on swipe apps and are now turned off from them. I see swipe apps become more niched during the next 10 years.
Gen Z is still tech dependent and I don't see them turning into great real world approachers. Millennials now in their 30s/early 40s aren't going to become better at approaching either.
Night game is now niched as compared to the era of Peak Mystery and Neil Strauss (late 1990s - mid 2000s).
When I first got out of college in 2005, it was the era of the pickup artist. By the time I graduated college in 2005, I had already read David DeAngelo's works. I had some familiarity with pickup and seduction by then. Strauss' "The Game" came out in September 2005, just months after my college graduation.
I moved to a new city after college as an unattached guy and immediately immersed myself in the nightlife venues of that city.
Bars and other nightlife venues aren't as important for initial interactions anymore. They still host 1st/2nd dates arranged via swipe app and social media DM. Maybe even some daygame arranged first dates.
I think there's a future in daygame but in a limited way. There's a lot of hype around run clubs right now as a daygame method. I don't know if that hype will materialize into anything. In the late 2000s/early 2010s, there was a lot of hype around kickball leagues and that trend has since faded.
Daygame will only improve if women stop using headphones/earbuds less outdoors and inside gyms. I don't see that happening for now.
I don't see things getting better for the average man (middle of the bell curve or mid-tier men) in the near future. These middle tier men are going to have to continue to keep bringing more to the table.
I'm a Millennial with Baby Boomer parents. All the adult figures I remember from my childhood were all Boomers.
When Woodstock happened in 1969, the oldest Boomers were 23. While there were many 18-23 year old Boomers at Woodstock, plenty of Boomers were still under 18 and were not able to attend Woodstock. There were plenty of 24-29 year old late Silent Generation people in attendance at Woodstock. Many of the Woodstock musicians, like Jimi Hendrix, were late Silents.
The Boomers pushed forth ideas of cohabitation without marriage (something gaining traction with the Silents before them). Getting high and getting laid wasn't unique to Boomers. However, I agree with your premise that Boomers became well known for them. The late Silents started this in the 1960s, but Boomers took it to the next level in the 1970s-1980s. Boomers were called the original "Me Generation" in popular culture in the 1970s.
The Boomers got a lot of privilege off of the successes of the GI Generation (1910s-early 1920s births) and a good portion of the Silent Generation (late 1920-1945 births). The Boomers selfishly took theirs, and subsequent generations got stuck cleaning up the messes, with each subsequent generation having less privilege.