Through Lola AI, I wanted to explore feelings I had after traveling to the Philippines for the first time to see family. I started by creating a framework focused on three themes of identity loss and grief following the passing of my grandmother. Prompted by the critique that AI creates art without a soul, I challenged myself to experiment with generative AI to see if it was possible to attempt to capture that essence, using the technology to create post-mortem data by cloning my Lola's voice and generating videos from old family photos to "channel" her presence. However, through four rounds of testing, I found that relying solely on AI distanced the project from its intent and felt too impersonal, proving that my genuine relationships and emotions could only be truly captured through real, human-generated moments. To clarify the narrative, I built a final storyboard that transitions from the speculative Gen-AI dialogue with Lola into a rush of authentic human content celebrating my Filipino-American identity, centering on the affirmation that I am "more than enough." Ultimately, Lola AI serves as a personal experiment into whether AI can be used as a tool to process grief and self-doubt, demonstrating that while the technology cannot replicate human creativity, it can act as a raw medium to help us express and navigate complex emotions we struggle to articulate.