In the Parallel Lives Plutarch does not absolve his readers of the need for moral reflection by offering any sort of hard and fact rules for their moral judgement. Rather, he uses strategies for eliciting from readers an active engagement with the act of judging. This study, building upon and verifying further recent research on the challenging and exploratory, rather than affirmative, moral impact that the Lives are designed to have on their readers, offers the first systematic analysis of the representation of 'experimental' moralism of Plutarch's Parallel Lives. It seeks to describe and analyse the range of narrative techniques that Plutarch employs to draw his readers into the process of moral evaluation and expose them to the complexities and difficulties involved in making moral judgements. Through illustrating Plutarch's narrative techniques, it also sheds significant light on Plutarch's sensibility to the artistic qualities of historical narrative as well as to the challenges and dangers inherent in recounting, reading, and evaluating history. Chapter 1 considers the interrogatory nature of the moralism of the Lives and their narrative sophistication, which the insights of recent literary theories can help us to unfold and analyse. Chapter 2 is concerned with Plutarch's projection of himself and his readers, and, more specifically, with the devices that Plutarch exploits to build his authority with his readers, establish their complicity, and draw them into engaging all the more actively with the subjects of his Lives. Chapter 3 examines how Plutarch's delving into the minds of the in-text characters generates in readers empathy that keeps them alert up to the end of the Life to the complex and provisional character of a clear-cut moralising judgement. Chapter 4 reflects especially upon Plutarch's tendency to refrain from offering an overall moral conclusion in the closing chapters of the biographies. It examines several closural devices (such as anecdotes, the aftermath of cities, literary allusions, and generalised moral statements) that are effective in drawing readers to review in retrospect moral themes and questions which matter to the book as a whole, and (in the case of the endings of the second Lives) help a neat transition to the final comparative epilogue (Synkrisis) - whenever this follows. Chapter 5 explores how the Synkriseis expose readers to the particular challenges involved in deciding an overarching concluding judgement. It also closely examines the books that (as they now stand) do not have a Synkrisis and makes the case that no 'terminal irregularity' can justify and explain any deliberate omission of their comparative epilogues. Finally, Chapter 6 focuses on Plutarch's essay On the malice of Herodotus and explores how far Plutarch's techniques in the Lives escape and how far they are vulnerable to the criticisms that Plutarch makes of Herodotus. This analysis brings together the main strands of the earlier chapters so as to illuminate further Plutarch's narrative strategies; it also discusses the possibility that Plutarch exploits the rhetorical agonistic framework of the essay in order to elicit a similar sort of attentive and acute reader response to historical narrative, as in the Lives, and to arouse awareness of the precarious act of exercising moral judgement.