Overtone Dating App: Why Justin McLeod’s AI Matchmaker Will Fail (According to a Real Matchmaker)
Justin McLeod/Former Founder and CEO of Hinge & Current Founder of Overtone
Justin McLeod, the founder and former CEO of Hinge, just announced he’s stepping down to launch Overtone, a new AI matchmaking app that promises to be “like working with an all-star personal matchmaker.” As someone who has worked as a professional matchmaker for over five years, I need to call out what’s really happening here: another tech CEO who has never done the actual work of matchmaking thinks he can automate away the humans who do it.
And here’s the uncomfortable truth: he’s going to fail. Not because AI doesn’t have its place in dating, but because he fundamentally misunderstands what matchmaking actually is.
What is Overtone? (Understanding Justin McLeod’s New AI Dating App)
According to McLeod’s announcement and coverage in Fortune and TechCrunch, Overtone is described as “an early-stage dating service focused on using AI and voice tools to help people connect in a more thoughtful and personal way.” The platform is backed by Match Group, which owns Hinge, Tinder, and OkCupid, and will operate independently starting in 2026.
McLeod’s pitch is that AI can now create “an entirely new way for people to find their partners that is far more personal, far more efficient, and far more effective. Think less like a social platform, more like the experience of working with an all-star personal matchmaker.”
There’s one glaring problem with this vision: McLeod has never actually worked as a matchmaker. He’s built platforms. He’s run a business. But he’s never sat across from a client who’s struggling to understand why they keep choosing the wrong partners. He’s never had to deliver hard truths that algorithms can’t compute.
The Problem with AI Matchmaking Apps
Here’s what McLeod conveniently glosses over in his announcement: dating apps already use AI extensively. Hinge has been implementing AI features for years. Tinder uses AI-powered matching. Bumble is developing what Whitney Wolfe Herd calls “the world’s smartest and most emotionally intelligent matchmaker.”
And you know what? People are more burned out than ever.
McLeod himself admits this in his announcement: “I also know firsthand how many daters out there are feeling burned out, overwhelmed and increasingly hopeless. In our current paradigm, daters are swiping through hundreds if not thousands of profiles to get to a date.”
Let me translate: AI-powered dating apps have created the problem that McLeod is now promising AI will solve. That’s not innovation. That’s just more of the same dressed up in new marketing language.
The data backs this up. Tinder has lost over 1.5 million paying users since 2022. A 2024 Forbes study found that three-quarters of dating app users experience “swipe fatigue.” Gen Z is increasingly disillusioned with online dating entirely, with many preferring to meet people in person instead.
The issue isn’t that the AI isn’t sophisticated enough. The issue is that algorithms can’t solve human problems.
What Real Matchmakers Do That AI Can’t
I’ve been working as a professional matchmaker in New York City for over five years. I run Met By Nick, a matchmaking and dating coaching business, and I co-founded QUALITY matchmaking services with my sister. I’ve worked with hundreds of clients, and I can tell you exactly what my job entails, and why no AI can replicate it.
Reading Between the Lines
When a client tells me they want someone “ambitious and successful,” I don’t just input those keywords into a database. I ask follow-up questions. I listen to how they talk about their ex-partners. I notice when they describe what they think they want versus what they actually need.
A client once told me she wanted someone “laid-back and spontaneous.” After three conversations, it became clear she actually craved stability and consistency; she’d just been burned by a controlling ex and was overcorrecting. An algorithm would have matched her with free-spirited creative types. I matched her with someone reliable and intentional who also knew how to have fun. They’re still together.
Identifying Self-Sabotaging Patterns
AI can’t tell you that you’re self-sabotaging. It can’t call you out when you’re choosing people based on chemistry while ignoring compatibility. It can’t sit with you through the discomfort of realizing that your dating patterns mirror your relationship with your parents.
I’ve had clients who swore they wanted a relationship but consistently chose emotionally unavailable partners. I’ve had clients who claimed to have high standards but were actually just afraid of intimacy. I’ve had clients who blamed the opposite sex for all their dating failures when the real issue was their approach.
A real matchmaker has those conversations. We hold up the mirror. We provide the accountability that makes people uncomfortable, because that discomfort is where growth happens.
Building Trust Over Time
Matchmaking isn’t a transaction. It’s a relationship. My clients don’t just hire me to make introductions. They hire me because they trust me to advocate for them, to be honest with them, and to understand the nuances of who they are beyond what they write in a profile.
That trust is built over weeks and months. It’s built through difficult conversations, through me getting matches wrong and learning from it, through me showing up consistently even when the process feels frustrating.
You can’t automate trust. You can’t code emotional safety. You can’t train an AI to know when to push a client and when to give them space.
Curating Matches Based on Judgment, Not Just Data
AI matches people based on data points: age, education, interests, location, maybe some compatibility algorithm. But human matchmakers match people based on judgment that incorporates factors no algorithm can quantify.
I consider how someone talks about their family. I notice if they light up when discussing their work or if they seem burned out. I think about whether their social circle would mesh with a potential match’s. I consider timing; is this person actually ready for what they say they want?
I once had two clients who looked perfect on paper: similar ages, both lawyers, both loved travel and trying new restaurants. But one was a people-pleaser who avoided conflict, and the other was direct to the point of bluntness. An algorithm would have matched them. I didn’t, because I knew that dynamic would create resentment within months.
Providing Coaching, Not Just Introductions
Here’s something McLeod doesn’t mention in his Overtone announcement: making introductions is maybe 30% of matchmaking. The other 70% is coaching.
I help clients improve their dating profiles. I role-play difficult conversations. I debrief after dates gone wrong. I help people understand why they’re experiencing dating burnout and what internal barriers are blocking them from connection.
When a client tells me a date “didn’t have chemistry,” I ask what that actually means. When they say they’re “too picky,” I help them distinguish between standards and fear. When they want to ghost someone instead of having an honest conversation, I push them to do the uncomfortable thing.
That’s the work. And it’s work that requires empathy, experience, and emotional intelligence; qualities that AI simply does not possess.
Why Tech CEOs Keep Getting Matchmaking Wrong
Justin McLeod isn’t the only tech founder trying to “disrupt” matchmaking with AI. Whitney Wolfe Herd, founder of Bumble, has proposed using AI dating assistants. Matthew Hussey, a dating influencer, is launching his own AI-powered platform. There’s a pattern here, and it’s revealing.
These people want the prestige of matchmaking without doing the actual work of matchmaking. They want to scale a service that fundamentally cannot be scaled without losing what makes it valuable. They see matchmaking as a data problem when it’s actually a relationship problem.
Let me be blunt: Justin McLeod could not do my job for one week. He couldn’t handle the emotional labor. He couldn’t navigate the nuanced judgment calls. He couldn’t manage the expectations of clients who are vulnerable and frustrated and desperately want to find love. He’s never had to tell someone that their approach to dating is the problem, not everyone else.
What tech CEOs understand is building products. What they don’t understand is building relationships. And you cannot automate relationships without stripping away the very thing that makes them meaningful.
McLeod writes in his announcement that “real relationships involve risk, vulnerability, effort and reciprocity and that’s exactly what makes them meaningful.” He’s absolutely right. But here’s what he misses: the matchmaking process itself requires those same qualities. You can’t outsource vulnerability to an algorithm. You can’t delegate emotional risk to AI.
The real motivation here is obvious: labor costs. A human matchmaker can only work with a limited number of clients. We require salaries, benefits, training, and support. An AI can “match” millions of people simultaneously with minimal overhead. That’s the actual innovation McLeod is selling; not better matchmaking, but cheaper matchmaking.
And here’s the thing: people will see through it. They already are. Dating app users are burned out precisely because they’ve been treated like data points for too long. They don’t want more algorithms. They want humans who actually give a damn.
The Future of Matchmaking: Community Over Algorithms
I’ve been writing extensively about where I believe matchmaking is actually heading, and it’s not toward AI. It’s toward community-based matchmaking; a model where individuals leverage their social networks to make introductions for people they know and care about.
This model works because it’s built on trust and accountability. When your friend introduces you to someone, there’s social capital on the line. The introduction comes with context, with endorsement, with a human who can vouch for both parties. It’s the opposite of swiping through strangers on an app.
The increasing secularization of society, the breakdown of traditional community structures, and the failure of dating apps have created a void. People are lonely. They’re isolated. They want to meet partners, but they’re exhausted by the algorithmic approach.
This is where real opportunity exists; not in building better algorithms, but in facilitating better human connections. Not in removing the matchmaker, but in empowering more people to become matchmakers within their own networks.
At Met By Nick, I’ve seen firsthand how powerful this approach is. The Single Saturdays events, I co-host with founder Natalie Cramer, create spaces for people to meet organically. My matchmaking work succeeds not because I have better data, but because I have better judgment. My coaching helps because I’m a human who can hold space for another human’s struggles.
That’s the future of matchmaking. And no amount of AI investment from Match Group will change that fundamental truth.
The Bottom Line
Justin McLeod’s Overtone will likely raise significant funding. It will probably get press coverage. It might even attract users who are curious about the “AI matchmaker” concept.
But it will fail to deliver on its core promise: providing an experience “like working with an all-star personal matchmaker.” Because that experience requires a human. It requires someone who can read emotions, provide accountability, build trust, and deliver hard truths with empathy.
McLeod is right about one thing: people are burned out from dating apps. But his solution, more AI, more algorithms, more automation, is just doubling down on the approach that created the problem in the first place.
If you’re tired of being treated like a data point, if you’re exhausted from swiping through profiles, if you want someone in your corner who actually understands the messy, human journey of finding connection, you don’t need an AI matchmaker. You need a real one.
About the Author: Nick is the founder of Met By Nick, a matchmaking and dating coaching business based in New York City, and co-founder of QUALITY matchmaking services. He offers premium matchmaking packages, dating profile optimization, and dating burnout coaching, and co-hosts Single Saturdays community events for singles.
