OCTOBER 17, 2025|ARTIFICIAL INTELLIGENCE
AI Matchmaking and How Expertise Is About to Be Scaled


There is an elite $2000-per-month matchmaking service called Three Day Rule that made news this week for their choice to create an AI matchmaking app based on their methods. In a dating world where some people are resorting to paying for a billboard to find a potential husband, people are desperate for alternatives. Talking about the value that a human matchmaker has always had over algorithms, founder Adam Cohen-Aslatei describes the reason for creating the app like this:
"He’s become convinced that [human] matchmaking is the most effective dating option out there. He argues that, on dating apps, users are looking for a match that meets their requirements on paper—standards that, oftentimes, are preventing them from taking healthy risks. Matchmakers are trained to take those preferences into consideration while also encouraging clients to try people slightly outside their comfort zone."
Users will report back on whether they feel this new app does truly recreate the human touch, but the story does point to a wider insight. The future of AI tools that people truly love and advocate for may all start this way: with a real human expert deciding to recreate the best of what they do in an automated way that scales. An AI tool that can make sculptures might be a fun but frivolous exercise. A tool created by a renowned sculptor, though, to bring their work to more people? That would be different.
Of course the question is whether enough real experts would be willing to have themselves duplicated (and perhaps eventually supplanted) in this way. Yet in the case of business experts, there are already prominent examples of brilliant minds allowing AI tools to be trained on their insights to allow them to coach more people than they ever could in person. Every expert that chooses to do this can legitimize the idea for another expert in a related (or unrelated) industry.
Rohit speaks on this topic. See his AI keynote.
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A Short Backstory Of This Blog
This is a blog about non-obvious ideas. Originally launched on the Typepad platform in 2005 as the Influential Marketing blog, the stories at first focused mainly on digital marketing while Rohit worked at Ogilvy Advertising. In 2015 Rohit officially rebranded to the Non-Obvious Insights Blog and published his WSJ bestseller Non-Obvious. For the past twenty one years, this blog has coined new terms, introduced future marketing practices and inspired the next generation of non-obvious thinkers and marketers.




