MIDWESTERN PASADENA follows Maisie Andrews who is home from college on her "winter break". As she gets settled in, she bumps into her neighbor, Angus, as they reconnect. Maisie finds out that Angus is taking a gap year to save up and travel. Throughout the story, Maisie and Angus share moments of reflection and reminisce about their shared past and discussing their dreams and aspirations. Maisie also struggles with the her feelings of uncertainty of the future. It is when Angus and Maisie are in their High School's parking lot when Maisie admits to Angus that she is not really on break and has dropped out, expressing to him that she feels unfulfilled and disconnected from living in the city. She even questions her major. Angus offers support and encourages Maisie to take her time and explore different paths until she finds what feels right.