Good point, Rollo is now 55 years old fighting against women young enough to be his daughters. Lauren Southern is a late Millennial (born 1995) and Brittany Venti is early Gen Z (born 1997). Rollo was already in the 2nd half of his 20s when both were born.
Getting too big seems to have been a problem for Roosh, Rollo, Roissy, Andrew Tate, and a few others. Even Mystery and Neil Strauss had some serious personal problems.
Tom Torero: Has a scandal surrounding non-consensual recordings. Dies unexpectedly. Family confirms his death was a suicide. Roosh: Sister dies of breast cancer. Leads to emotional breakdown. Has a religious conversion and condemns pickup, seduction, and all non-marital sex. Neil Strauss: Was...
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The first half of the 1990s is the answer to all 3 of those questions. Also, it was a lot more difficult to arrange multiple first dates in a short period in the 1990s as compared to today. With swipe apps in the 2010s, I could arrange 3-4 first dates in a week. I might have even been able to double book, which I never did. I did arrange first dates on 3 consecutive nights. Try arranging first dates on 3 consecutive nights without using swipe apps or sending a massive amount of DMs on Instagram.
It must be pointed out that tech-based methods are excellent at producing low-quality dates, ones of the "one date, no sex, no second date" variety.
It is better to arrange fewer dates but have a higher percentage of dates result in sex and/or extended relationships.