From trading goats in Mesopotamia to ghosting on Bumble—romance has come a long way.
In this episode, Ryan breaks down the bizarre, hilarious, and often depressing evolution of dating across history. From arranged marriages and WWII love stories to dating cards, personal ads, and Tinder fatigue, he explores how love has been bought, sold, scheduled, and swiped for centuries.
You’ll hear about:
Cultural rituals that make The Bachelor look tame
The moment dating left the home (and entered the diner)
How AI and algorithms are now the matchmakers
Why Gen Z might be the loneliest—and pickiest—generation yet
Plus, a few awkward stories from Ryan’s own history that prove love may be eternal, but dating? A mess.
🎙 Chapters:
00:00 - Ancient Courtship & Awkward Teen Phone Calls
05:01 - Love Stories from WWII to Gen Z
15:54 - Rise of Dating Apps & AI in Romance
20:05 - High Expectations & Online Letdowns
28:58 - First Dates Gone Wrong
🎧 All links → linktr.ee/stayinthegraypodcast
