Dating in 2026: A Strategy & UX Audit

By Shannon Weber & Lizelle Rademan

There’s something quite fascinating that happens when the Head of Strategy and the Head of UX look at the same problem: they rarely agree on why something is broken, but almost always agree that it is.

Which is how, somewhere between a discussion about brand positioning and a slightly heated debate about broken user journeys, we found ourselves analysing… dating.

That wasn’t our intention, of course. But once you’ve spent enough time diagnosing complex processes and building functioning systems, patterns start to reveal themselves everywhere and often in places you didn’t quite expect. So when it came up in conversation, the conclusion was difficult to ignore:

Modern dating isn’t complex. It’s just badly designed.

It’s a positioning problem,” says Strategy, confidently, as if this explains everything.

“On the contrary,” replies UX, “it’s actually a user experience failure.”

However, as it turns out, it’s both.

From a strategic perspective, the issue begins with how people present themselves.

Everyone arrives carefully packaged as a premium offer; ambitious, adventurous, emotionally aware, deeply into wellness, possibly running a business, definitely regularly going to the gym and yet, somewhere between the first interaction and the third conversation, the narrative begins to… unravel.

There is, quite simply, a disconnect between what’s promised and what’s actually delivered. In a strategy context, we would simply call that what it is – poor positioning.

From a UX perspective, however, things deteriorate even faster. Because before you can commit to anything, you first need to observe behaviour, and the behavioural patterns are frequently concerning:

Does the subject express interest, ask questions, listen, engage, build on the conversation? Or does the entire interaction resemble a loading screen from 2004?

“Good morning!”

“Hey.”

“So, what you doing today?”

“Nothing.”

At this point UX is often tempted to close the laptop, and log the issue as a critical failure in basic interaction design.

But that might be bit premature, so before that happens we would normally try to carry out an interface evaluation; not skimming the surface, but in-depth, as we would with any complex system.

There are, after all, certain baseline standards. Is there:

  • A degree of order?
  • A sense of coherence?
  • Evidence that the system is being maintained?

Because while a polished interface doesn’t guarantee a stable backend, a chaotic one is rarely hiding anything impressive beneath the surface.

Supposing it passes, next comes feature evaluation, which is where things tend to become particularly revealing.

There are, of course, the core features we’re all quietly hoping for; kindness, emotional intelligence, humour, a general ability to function as an adult human without excessive external support.

And then there are the features that, once identified, are flagged immediately.

  • Over-explaining
  • Under-listening
  • Selective communication

And if any prompt triggers the familiar ‘I’m just not great at this’ response, it’s going to raise a red flag, because just like in any product environment, this wouldn’t be seen as a personality trait, but as a system defect requiring urgent attention.

Eventually, as with any audit, the conversation arrives at the only question that really matters: does this system improve the user’s life?

Because the best-designed experiences – whether in products, platforms, or relationships – rarely feel complicated:

They are intuitive, consistent and low-friction.

They don’t require constant interpretation, troubleshooting, or emotional debugging.

And ideally, they operate without introducing unnecessary chaos into an otherwise well-functioning environment.

Which is, perhaps, why Strategy and UX so often arrive at the same conclusion, even when they take entirely different routes to get there.

Because whether we are looking at a business, a digital platform, or even the modern dating landscape, the principles remain the same:

Understand the user needs, fix the architecture and design something people actually want to engage with. It’s really that simple!

Incidentally, if your business is starting to feel a little like a system with too many workarounds, unclear messaging, and the occasional unexplained breakdown, it might be time for an audit.

We’re pretty good at those, and if nothing else, we promise significantly fewer bugs.