Sentimental fiction is nowadays often seen as the province of a femininity slowly asserting itself against all patriarchal odds. Pamela and Clarissa have become the heroines in this one-sided story. However, sentimental fiction and the philosophy that goes hand in hand with it also had important effects on the reformulation of acceptable modes of masculinity. Harley, the protagonist of Mackenzie’s seminal short novel, is such a transitional figure who is torn between privilege and individual virtue, rationality and feeling, expected strength and appropriate weakness. In him we can see a trial run of modern masculinity – or rather of the various acceptable shapes of modern masculinities. He also offers a suitable illustration of the transition from Neoclassical to Romantic to bourgeois masculinity. The fact that he does not survive his own story but is torn apart by his contradictions points towards impasses in masculine roles with which we are still struggling today.