The article considers how Joanna Baillie’s concept of “sympathetick curiosity” informs contemporary discussions about emotion regulation. By focusing on Baillie’s De Monfort (1798) and Orra (1812), the article argues that regulatory flexibility is a learned skill that can be improved by actively engaging sympathetic curiosity. Baillie insisted that her plays had pedagogical value and that having audiences watch them would help them learn how to avoid the destructive nature of the passions. Working with Bonanno and Burton’s (2013) model of regulatory flexibility, the article demonstrates the importance not just of inherent differences in emotion regulation but also of learning opportunities individuals engage to develop it. In particular, the article presents a model of how people learn through narrative simulation, drawing on the work of Romantic writers and current critics as well as cognitive psychologists and neuropsychologists. Consideration is then given to how watching protagonists’ manifestations of and responses to an unfolding passion helps audiences learn to develop their regulatory flexibility.

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