AI matchmaking is having a moment.

Every few months, there’s a new service promising to solve what dating apps can’t. They use machine learning, personality quizzes, or digital “compatibility maps” to take the guesswork out of finding your person. The idea is simple: if we could just meet the right person, everything else would fall into place.

It’s an appealing promise. Swipe fatigue is real. But after years of working as both a dating coach and a professional matchmaker, I can tell you — the matching part has never been the real problem.

1. Why Matching Isn’t the Real Problem

During my time at Three Day Rule, I met hundreds of successful, interesting singles who wanted real connection. I matched people based on their values, interests, and lifestyles. Sometimes, they even looked perfect together.

And yet, it often didn’t work.

You can match two people on paper and even in photos, but you can’t predict what happens when they meet in person. Chemistry doesn’t care about compatibility scores. Attraction is human, not statistical.

What I eventually realized is that people already match themselves pretty well on dating apps. They know what they like and what they don’t. The problem isn’t that they can’t find a match — it’s that they don’t know what to do once they have one.

2. The Database Dilemma

All matchmaking systems, whether human or algorithmic, face the same technical limitation: the size of the database.

Even the best AI can’t make magic out of zero data. If a database has 100,000 users but only a few are interested in you, it doesn’t matter how sophisticated the filtering is — you’ll still end up with nothing.

And ironically, people don’t actually want fewer choices. They want better choices. They want to feel desired and hopeful. Running out of profiles is far more discouraging than swiping through people you don’t like.

Dating, at its core, is a numbers game — but one that depends on timing, flow, and luck.

You want to be active on the largest and most popular dating apps - namely Hinge and Bumble. This is where the newly single go and where the best new matches will appear.

3. The Real Solution: Match Yourself Better

Instead of trying to replace dating apps, I believe in learning to use them better. That means writing a stronger profile, communicating with intention, and understanding how to pace yourself emotionally.

These are the skills I work on with my clients every day. Once you understand what makes you interesting, and how to show that clearly, the right people will start to find you.

AI can help you automate your inbox or summarize your DMs, but it can’t teach you how to be curious, grounded, or self-aware. It can’t tell you why you ghost people when things get close, or why you lose interest after the second date.

Those are deeply human questions — and they require a human to help you unpack them.

4. The Human Factor

I’ve had clients who could get all the matches they wanted, but none of them turned into dates. The problem wasn’t their profile — it was their communication. One client didn’t know how to take control of the conversation. Another couldn’t make a decision about who to see again and ended up paralyzed by indecision.

These issues don’t get solved by smarter matching. They get solved by practice, reflection, and honest feedback.

That’s what dating coaching is — not advice from your friends or a pep talk from a stranger online, but a structured process of learning how to date better.

5. A Call for Depth

I love what the tech industry is trying to do. I really do. The intention is good — to make dating simpler, faster, less painful. But dating isn’t supposed to be frictionless. It’s supposed to teach you something about who you are.

AI can optimize everything except the parts that matter most: attraction, confidence, vulnerability, timing. Those can’t be predicted. They can only be learned.

That’s where coaching comes in.

How I Can Help

I’m a dating coach, and I love what I do. My focus is to help you become your own best matchmaker — to teach you how to date with clarity, confidence, and intention.

Modern dating requires skill and practice. Learning how to write a great profile, text effectively, and build connection in person are all part of that.

I’m here to help.

For more information, please visit www.agoodfirstdate.com or email grace@agoodfirstdate.com.