The film explores the lives of two individuals, each with a unique obsession with the 1980s pop star Tiffany. Jeff Turner is a 50-year-old man from California who has been devoted to Tiffany since her early career. He believes that he shares a deep spiritual bond with the singer and insists they are meant to be together. Jeff's obsession leads him to travel across the country, attending her concerts and seeking chances to meet her in person. His life is consumed by collecting memorabilia, analyzing her songs for hidden messages, and speaking about their presumed connection to anyone who will listen. Jeff is unwavering in his belief that Tiffany reciprocates his feelings, although his friends and family grow increasingly concerned about his behavior.

Kelly McCormick is a woman in her 30s living in Colorado, who also harbors a deep infatuation with Tiffany. Kelly's life revolves around the singer, whose music played an immense role in pulling her through tough times. Unlike Jeff, Kelly never attempts to personally contact Tiffany but instead channels her energy into creating a fan-zine dedicated to the star. As her devotion intensifies, it becomes clear that her attachment is not just admiration but a deep-seated obsession influencing every aspect of her life. Through interviews and intimate glimpses into their daily routines, the film paints a portrait of how these fixations shape Jeff's and Kelly's lives, both property and relationships, and raises questions about the nature of fandom and personal connections with celebrities.