Jack Dorsey's Block Built an AI Model That Talks Like an Awkward New Friend

You really have to hear these conversations with Block's new Dessa AI model.

A Different Kind of Conversational AI

By Jay Peters

In a 2026 AI landscape dominated by polished, hyper-capable assistants, Jack Dorsey's Block has taken a deliberately different path. The fintech company has introduced Dessa, a new AI model designed to converse with users less like a polished assistant and more like an awkward new friend—an intentional departure from the frictionless, overly agreeable tone that has become standard across the industry.

Block is inviting people to listen for themselves to sample conversations with Dessa, which showcase the model's distinctive, offbeat personality. Rather than the crisp, efficient responses users have come to expect from mainstream chatbots, Dessa's exchanges lean into hesitation, curiosity, and a certain endearing clumsiness—qualities that make the interaction feel more human, if a little unpolished.

Why an Awkward AI?

The move reflects a broader shift in how companies are thinking about AI personality. As conversational models have become ubiquitous and increasingly uniform in voice, some developers are experimenting with deliberate imperfection to build rapport and differentiate their products. Dessa appears to be Block's bet that relatability—rather than raw capability or seamlessness—can be a compelling differentiator.

What to Watch

Block has yet to detail the full scope of what Dessa will power or how widely it will be deployed. For now, the company is letting the conversations speak for themselves. As the AI industry continues to mature in 2026, Dessa stands out as a reminder that not every model needs to sound perfect—sometimes sounding a little awkward is the whole point.

via The Verge AI