Abstract

In this paper, I explore a noted empirical link between regret and insomnia. Drawing on Brian O’Shaughnessy analysis of wakeful consciousness, I sketch three candidate ways of excavating a conceptual connection. Regret involves a certain kind of temporal orientation that, for O’Shaughnessy, only the state of wakefulness makes possible. Regret involves mental activity – it is productive of and precipitates patterns of counterfactual thought and imagining. Further, picking up a cue from Bernard Williams’ celebrated conception of agent-regret in ‘Moral Luck’, sometimes the mental activity that occurs in regret is affective and expressive – as I argue, it is expressive of the wish that things were otherwise were satisfied now. Finally, I take up the puzzle as to why occurrent regret is not merely incompatible with sleep – insofar as it necessitates wakefulness - but may preclude falling asleep and I offer a tentative solution, focusing on the self-conscious character of occurrent regret.