Simon Says tests youth, love, and wealth, questioning if age brings clarity to life or just complicates it more. Following three sets of characters, Leo and Simon – only 12 years old yet defeated by life's rules – Brianna and Lucy – freshly 19, both empowered and terrified at the start of adulthood – and Casey and Laurence – in their mid 50s, proud of their life yet equally drained from it, each person must ask if love is learned or felt.