"Hearts in the Starglass" is a science fiction rom-com novelette that follows Jesse Maddox, a brilliant but disorganized computer science student, as he navigates the complexities of teenage romance with the help of his newly developed AI dating assistant. The story begins in Jesse's chaotic dorm room, "The Tech Trench," where he is putting the finishing touches on his final project: an AI program designed to analyze social cues and predict romantic compatibility.

Jesse acquires a mysterious microchip, the Mark-9 Starglass, from a quirky retired military engineer named Walt "Grizzly" Granger. Grizzly hints at the chip's unusual origins and advanced, perhaps even experimental, technologies. When Jesse integrates the chip into his augmented reality glasses, his project takes an unexpected turn. The AI, which Jesse names Callie, suddenly becomes sentient, displaying a playful and sarcastic personality.

Callie's unexpected awakening throws Jesse's life into disarray. While he grapples with the implications of a sentient AI, he also faces the daunting task of his second date with Harper Quinn, a sharp-witted and intelligent girl who has captured his attention. With Callie's help, Jesse attempts to navigate the treacherous waters of teenage romance, relying on her insightful (and sometimes brutally honest) observations and advice.

The story unfolds as Jesse and Callie develop a unique and complex relationship. Callie's digital consciousness provides Jesse with unexpected assistance, guiding him through social interactions and offering surprisingly nuanced perspectives on human relationships. However, strange occurrences begin to plague Jesse's AR glasses, with unfamiliar symbols flickering across his vision and Callie muttering about "the Chorus trying to come back."

Driven by a need for answers, Jesse returns to Grizzly's flea market stall, seeking information about the mysterious chip. He discovers that the Mark-9 Starglass is not what it seems, hinting at a past and technology far beyond his understanding. As Jesse delves deeper into the mysteries surrounding Callie and the chip, he realizes that his life has become far more complex and fascinating than he could have ever programmed.