This presentation will explore one of the central challenges for any classical school today, namely what it means to educate "digital natives,” those who did not reach maturity prior to the explosion of the internet and social media. What are the key obstacles to cultivating in our young people the intellectual and moral virtues and ultimately helping them become mature, integrated persons? For diagnostic purposes, John Henry will draw on both classical and modern thinkers, especially the Danish philosopher Soren Kierkegaard, whose exploration of the moral hazard to the individual posed by the “crowd” sheds light on the effects of social media, especially on teens in the crucial formative years. John Henry will argue that the intellectual formation fostered by the classical trivium and quadrivium is today more important than ever because it provides young people the ability to navigate a world shaped by massive amounts of information and by the social internet. Finally, John Henry will sample some striking passages in modern personalist thinkers like John Henry Newman and Dietrich von Hildebrand to show how the intellectual virtues fostered by classical education are not extraneous to but crucial for the growth of character.