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How do we understand and represent ourselves and others in the realm of digitally mediated love and intimacy? Through interdisciplinary readings and hands-on projects, this First-Year Seminar explores the intersection of technology, identity, and relationships, both before and after the advent of the computer age. Seemingly inescapable, computational systems shape the way we connect. However, algorithms, artificial intelligence, and search engines are not neutral—they are deeply entangled with questions of gender and sexuality. Amidst the promises of revolutionary changes brought by technological progress, we will critically examine how digital platforms both challenge and reinforce traditional norms around love, desire, and identity.