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Dating hasn't always looked like this.
Over the last 100 years, American dating has gone from calling cards and milkshake dates to personal ads, nightclubs, dating apps, swiping, and algorithms.
We have more choice, access, information, and control over our love lives than ever before. So why does modern dating feel so exhausting?
In this episode of The Realistic Romantic, Drew takes us through 100 years of dating history to understand how we got here and why every generation eventually rebelled against the dating rules that came before it.
Plus, we're talking about the rise of IRL singles events and "soft socializing." Could meeting strangers in real life be the next dating rebellion?
In This Episode
• 100 years of American dating history
• How the modern first date was born
• Intentional dating vs. optimized dating
• The rise of IRL singles events and "soft socializing"
• How to make dating feel more fun again
Chapters
00:00 Did Dating Used to Be More Fun?
02:12 Are We Entering the IRL Dating Rebellion?
04:53 Dating History 101: 100 Years of First Dates
24:31 How to Make Dating More Fun
References & Resources
📚 The Complex History of American Dating | JSTOR Daily https://daily.jstor.org/the-complex-history-of-american-dating/
📖 From Front Porch to Back Seat: A History of the Date | Beth Bailey Referenced throughout the episode as a key scholarly history of American dating.
🧩 America's Meetup Explosion | Axios https://www.axios.com/2026/08/17/meetup-dating-gen-z-loneliness
💻 Online Dating Research | Pew Research Center https://www.pewresearch.org/short-reads/2020/02/06/qa-how-and-why-we-studied-online-dating-in-the-u-s/
Connect
🌐 Website https://www.therealisticromantic.com
❤️ App https://studio.com/drew-henry/realisticromantic?c=9fvpYitc
📖 Substack https://therealisticromantic.substack.com
📸 Instagram https://www.instagram.com/therealisticromantic
🎵 TikTok https://www.tiktok.com/@therealisticromantic
▶️ YouTube https://www.youtube.com/@therealisticromantic
📩 Email: heyrealisticromantic@gmail.com
And do you think dating actually used to be more fun? Let me know in the comments.
Date without delusion.
#DatingHistory #ModernDating #DatingApps #DatingAdvice #OnlineDating #FirstDates #IRLDating #DatingCulture
