It wasn't much better in terms of attracting women as an unattractive male - despite iPhones, Tinder, and social media not existing back then. Women were just as stuck-up in my presence back then as they are now.
Culturally, it was nearly as degenerate as MTV spring break videos will show you. Hookup culture was alive and well back then, only the main channels for obtaining a ONS were nightclubs and parties instead of Tinder. Shows like Sex and the City were popular among women and influenced them.
Music was terrible in the late-1990s and early-2000s compared to the early-to-mid 1990s. Shitty nu-metal bands dominated the rock scene and rap had gotten more commercialized since the early-to-mid 1990s glory years.
I didn't care for the gaming of that era either. I preferred the old classic NES/SNES games of my childhood and modern games that came afterwards.
Dial-up internet was the norm back then and was nowhere near as fast as today's broadband internet. Nevertheless, the internet was a novelty at the time and I would say the decade between 1998-07 was the glory years of internet culture.
My favorite era from a cultural standpoint was the early-to-mid 1990s, but even that time period was marred by the relentless bullying I received in middle school and the first few years of high school that irreparably damaged my self-esteem.