The Golden Age of AI Matchmaking

Not so long ago, the first question people asked about “AI matches” was: “Isn’t that just for dating?” And it was a fair question because, for years, the notion of computers matching us with people seemed relegated to romantic apps. We saw how those apps could look at piles of data about us and guess who we’d click with. But from a business standpoint, it always stayed rudimentary: you’d get a recommendation to “connect with John because you both have marketing in your profile.” That was about as deep as it went.

Something happened in the last five or six years. It wasn’t a single event, but a confluence of better AI models and more abundant personal data. Suddenly, a matching system could do more than just look at job titles. It could parse your writing, your goals, maybe even sense your personality from the signals you left online. It could figure out that you really like creative marketing campaigns—particularly for direct-to-consumer brands. Meanwhile, it notices a founder who’s trying to pivot her apparel startup to a direct-to-consumer model. Voila: you two get introduced, and it doesn’t feel random at all. In fact, it’s so specific you both have that uncanny reaction: “Wait, how did you know we’d get along?”

I call it “the golden age of AI matchmaking” because this jump in specificity is making old school, guess-and-check networking obsolete. Before, we’d spam a bunch of possible leads or rely on generic speed-dating style events. We might meet a good match one out of twenty times. Now, the AI systems are getting the success rate so high it feels like skipping all the filler. And they keep getting better each time we confirm, “Yes, that was a great conversation,” or “No, that didn’t work for me.” They learn.

There’s also a deeper shift at play: the acceptance of letting an algorithm handle introductions we used to want a “human touch” for. We used to think only a personal friend who truly knows us can help us meet interesting people. And if you have a well-connected friend who’s thoughtful about these intros, that’s amazing. But that’s out of reach for most of us. AI is like an infinitely scalable, always-on version of that thoughtful connector friend. It sifts through possibilities, weighs intangible variables, and suggests a conversation. The best part is, it can do it for thousands (or millions) of people all at once.

Why now? Because we’re living in an era of deeper data. As more of our professional lives flow into digital channels, AI has a richer portrait of who we are, what we want, and how we interact. It’s not just about “he’s a product manager” or “she’s in finance.” You might mention in your profile that you started as a teacher, or you’re trying to learn about XR technology on the side. The AI picks up on that, sees someone else who’s an XR hobbyist, and finds the synergy. We’re bridging hidden similarities that typical job titles or LinkedIn filters never surface.

The irony is that “cold networking” used to feel so tedious precisely because it was random. We’d send out requests, not knowing if the recipients cared about the same topics. But now, the biggest leap forward is that the randomness can be replaced with “targeted serendipity.” By letting an AI do the heavy lifting, we’re stepping into a future where it’s normal to have a curated conversation queue. And we’re seeing it in everything from specialized founder communities, to investor matching, to employee mentorship inside large companies.

I think the reason we call it a golden age is that these benefits are still somewhat new to many people. In time, we’ll probably take it for granted. We’ll assume that, of course, an AI can figure out who we should meet next and set it up automatically. But right now, it’s still fresh enough to feel like magic. And if you’re an early adopter, you gain a massive edge. In business, an edge in meeting the right people is an edge in everything. It’s how you discover new solutions, new hires, new directions. It’s not an exaggeration to say that finding the right collaborator can alter the trajectory of your entire career. And if an AI can make that meeting happen two years earlier than random chance would have, how many opportunities does that open up?