Doris, a quirky and eccentric woman in her sixties, has spent her life taking care of her mother and working a monotonous office job. After attending a self-help seminar, Doris becomes infatuated with John, a much younger, handsome new art director at her company. Encouraged by her closest friend Roz and inspired by the seminar's teachings, Doris invents ways to attract John's attention and integrate into his social circle, despite their significant age gap. This leads her to make bold fashion choices, create elaborate fantasies, and explore the world of modern technology and social media to connect with him.

As Doris's efforts draw John closer, she finds herself navigating the complexities of workplace dynamics, friendships, and her own long-suppressed desires. Her interactions with John lead to personal growth and self-discovery, revealing both the joy and challenges of pursuing one's dreams later in life. All the while, Doris struggles with family issues, especially with her practical brother Todd and his wife, who are urging her to declutter her life. The unfolding events push Doris to confront reality and reconsider what truly makes her happy.