Loving Annabelle is the controversial story of a Catholic Boarding School teacher, Simone Bradley (Diane Gaidry), who has an affair with her female student, Annabelle (Erin Kelly). Inspired by the 1931 German classic, Maedchen In Uniform, director Katharine Brooks's Loving Annabelle gives a modern telling of the "forbidden love" story that continues to be controversial to this day.

Simone is Saint Theresa's prized young poetry teacher who finds peace and security within the boarding school's walls. Surrounded by a lush atmosphere with little conflict, Simone has settled into a life of comfort and purpose educating her young female students.

Annabelle is a charismatic and enchanting new student who quickly draws attention for her rebellious behavior. Fearing Annabelle will influence the other students, rigid Headmistress (Ilene Graff), instructs Simone to keep an eye on Annabelle and get her under control.

Simone, however, quickly learns that the real challenge is not Annabelle's behavior but the attraction budding between the two. As Annabelle pursues her teacher, she unleashes the passion that has been locked deep inside Simone, who must decide whether or not to enter into an affair that could cost her everything.