Where Grief Meets AI: Arianna Wellmoney on Storytelling, Memory, and the Ethics of Holding On

Arianna Wellmoney’s Rip Jabari You Would’ve Loved the Apple Dance is a deeply resonant exploration of grief in the digital age, born from the tension between comfort and unease in interacting with those we’ve lost. Evolving from stage to screen and now into a web series, the project highlights her commitment to emotional truth while examining how technology reshapes memory, connection, and mourning. As an independent immigrant artist, Arianna continues to push boundaries — creating space for complex questions around love, loss, and dependence, while proving that powerful, meaningful storytelling can be built outside traditional systems.

Arianna, your project “Rip Jabari You Would’ve Loved the Apple Dance” has gained powerful momentum—can you share what originally inspired the story and why this felt like the right moment to tell it?
The project really started from a mix of curiosity and discomfort. I was thinking a lot about how we process grief today, especially in a world where technology is increasingly present in our most intimate spaces. The idea of being able to “interact” with someone we’ve lost felt both comforting and deeply unsettling to me. That tension became the foundation of the story.

At the same time, I was noticing how often we avoid fully sitting with loss. There’s this impulse to move on quickly, to find solutions, to fix the pain. This piece asks: what happens if we don’t let grief be temporary? And what happens if technology offers us a way to bypass it? It felt like the right moment to tell this story because AI is no longer abstract: it’s here, and it’s already reshaping how we connect, remember, and mourn.

The piece has evolved from a stage play under Wellmoney Productions to a play-film hybrid—what did that creative evolution teach you about storytelling across different mediums?
It taught me that the core of the story has to remain emotionally truthful, but the way you deliver that truth can change depending on the medium. Theater demands presence. It thrives on immediacy and the shared experience between actors and audience. Film, on the other hand, allows for intimacy in a different way: with close-ups, editing, and control over perspective.

I’m still writing the web series adaptation of it and adapting the piece forced me to rethink rhythm, pacing, and even silence. Moments that lived in dialogue on stage sometimes become visual in the film version. It also makes me more aware of what each medium does best, and how to lean into that rather than trying to replicate one within the other.

At its core, the project explores grief, memory, and artificial intelligence—how did you balance the emotional intimacy of loss with the ethical questions surrounding technology and digital resurrection?
For me, the emotional truth always came first. If the audience doesn’t believe in the relationship, the ethical questions don’t land. So I focused deeply on building the bond between these characters (and my cast) , the history, the humor, the specificity of our connection.

Once that foundation was there, the ethical questions could emerge more organically. I wasn’t interested in presenting clear answers, but rather in creating space for discomfort and questions. Jabari, the AI robot, isn’t framed as purely good or bad, it reflects the desires and limitations of the people using it. That ambiguity felt important, because that’s how these technologies exist in real life.

As an independent, self-funded immigrant artist, what did it mean to receive this level of awards recognition, and how did it validate your approach to building work outside traditional systems?
It meant a lot, especially because the journey has required a lot of trust in myself and in the people around me. Being an immigrant artist often means building without a safety net or a clear future (“Will I be in the country 6 months from now? How do I make art not knowing what the future holds?”) financially, structurally, and sometimes even culturally. So to have the work recognized in this way felt like a reminder that there is space for stories built outside traditional systems.

More than validation, it felt like encouragement to keep going in the same direction. To keep prioritizing collaboration, community, and storytelling that feels honest to my perspective. It reinforced that I don’t need to wait for permission to create meaningful work! I can build it with the resources and people I have.

Now that you’re developing Rip Jabari into a web series, what new layers of the story are you most excited to explore in an episodic format, especially around AI and the complexity of grief?
The episodic format will allow us to slow everything down (while making the pace really fast) and really live inside the consequences. In a play or a film, you’re often moving toward a resolution. In a series, you can sit in the in-between, in the moments where grief resurfaces in unexpected ways.

I’m especially excited to explore how the relationship with Jabari evolves over time. Not just emotionally, but psychologically, how dependence can form, how memory can become distorted, and how the line between honoring someone and holding onto them too tightly starts to blur.

It also gives us space to expand the world beyond the central relationship. We can explore how different people respond to this technology, how it affects communities, and how personal grief intersects with something much larger and systemic. That scale is something I’m really excited about!!

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