Fives are heady types, supreme thinkers and philosophers, as Will confirms his "endless curiosity" for books and learning, and returning to school whenever he hits an existential crisis. Enneagram expert Ian Cron describes Fives as the most misunderstood type, people with emotions beneath their intellectual exterior, and Will confirms his journey with processing difficult emotions. He shares the appeal of intellectual attraction versus physical attraction for the Five, and he explains how his problem-solving nature wanted to "fix" his "gay problem" in adolescence. During stress Will admits getting disorganized and clingy, but during security he's passionate about strengthening the people around him – where, as a pastor, his Five-ness particularly shines. During times of doubt and questions, Will returns to the Gospels and his love for how Jesus makes sense of this world.