In this brief but broad-based reflection on homosexuality and gender identity as personally experienced by the author, he describes a shocking encounter with a high school friend who came out to him as gay, arousing visceral dread and revulsion for the idea of being wanted, sexually, by another man. At the same time, he was aware of the painful aloneness from which his friend was reaching out for connection and acceptance by someone he deeply respected and knew was straight. It took time and much help from both Psychoanalysis and Christianity to access and integrate the author’s feelings of love and hate, desire for and fear of his own father who died after he expressed his all-out infantile, destructive rejection. It is important, he believes, to bear not-knowing and identity-confusion to understand both homosexuality and homophobia on the way toward viable forms of homo- and hetero-philia.