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Loving Annabelle was inspired by the 1931 German classic Maedchen in Uniform.
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Director Katherine Brooks's motion picture directorial debut.
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In the scene where Simone sits in the closet, looking at photos of her former lover, the photos are actually pictures of director Katherine Brooks.
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The green couch in Simone's apartment is director Katherine Brooks's personal sofa.
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Actress Erin Kelly was approached by director Katherine Brooks randomly in a theatre audience and began working on the script/movie with her for three years before the movie began production. Actress Diane Gaidry was hired three days before the movie began production.
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The movie was made in three weeks.
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In the director's commentary, Katherine Brooks stated that she taught actress Erin Kelly how to remove "Simone's" bra with one hand so the choreographed sex scene would look natural.
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In the scene when Annabelle leaves the end-of-year ball with St. Peters to retrieve her guitar and the music for a song she wrote earlier, a poster is plainly visible on the wall above her bedside table, featuring the band that originally wrote and performed the song she is about to sing.
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During Annabelle's first English class with Ms. Bradley, random quotes and poems are written on the chalk board, which becomes visible while Ms. Bradley quotes a poem by Walt Whitman. During this time, the lyrics "open your heart, catch my disease" followed by "B. Lee" from Ben Lee's 2005 single "Catch My Disease" can be seen in the lower left corner of the board, written in yellow chalk. This is presumably a joke quote, that has no relevance to the scene.
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