Episode 81--X & Y On The Fly--Dating And Relating: The Last 25 Years

About this episode

The episode reflects on the changes in dating and relationships over the past 25 years, contrasting past norms with today's practices.

Exactly 25 years and one week ago, everyone's attention was on whether or not the dreaded Y2K bug was going to crash the world's computer systems and make planes fall out of the sky. And even as we partied like it was 1999, nobody's nose was buried in their smartphone because those hadn't come out yet. People weren't even texting each other. After all, if on the off chance you had texting on your phone, every message cost like sixty cents. Online dating was in its infancy, but already stigmatized as if any users were desperate losers who 'liked pina coladas'. Indeed, if a guy wanted to ask a woman out the best way to do that was in person (go figure), because picking up the phone and being confronted with an answering machine was just too stressful. But at least actual dating was still a thing rather than simply 'hooking up' or 'hanging out'. Nevertheless, getting quality dating advice from, well...anywhere? Forgettaboutit. Self-help of any kind on the still narrowband Internet was practically unheard of. Even what would become the PUA movement was still limited to 'underground' keyboard jockeys in chat rooms (!) trying to figure out tricks to 'game' women with. Social media was…

People in this episode

Hosts: Scot McKay, Emily McKay

Topics covered

• dating
• relationships
• technology
• social change
• cultural shifts

Keywords

• dating
• Y2K
• relationships
• technology
• social media
• cultural shifts
• dating advice

More episodes of X & Y On The Fly - Dating Podcast | Love | Sex | Relationships

• Episode 87--X & Y On The Fly--The Evolution Of Dating Advice · December 26, 2026
• Episode 89--X & Y On The Fly--You Never Outgrow Flirting · May 15, 2026
• Episode 88--X & Y On The Fly--The Seasons Of Marriage (20 Years In!) · March 6, 2026
• Episode 86--X & Y On The Fly--What If You're Disappointed? · October 17, 2025
• Episode 85--X & Y On The Fly--Dating, Relating And Pets · August 8, 2025
• Episode 84--X & Y On The Fly--Dealing With Your Ex (Or Theirs) · May 30, 2025