AI can write poems, print paintings, and write code—but can it help us understand who we really are? In an age where technology can both amplify individuality and flatten us into data points, we explore the rise of Digital Romanticism: the quest to use AI for self-discovery rather than self-erasure. From dream analysis to founder psychology, this session brings together a techno-philosopher, a polymath turned AI founder, and a startup sage to unpack the tension between nuance and homogeneity. Will AI be our mirror or just another echo chamber? Let’s find out.