The relation between masculinities and care is theoretically and empirically researched via the term caring masculinities. Until now, research has focused on adult men and has not explored the question of how care orientations are developed through processes of socialization. This article, therefore, presents findings on care experiences of adolescent boys. Based on 89 qualitative interviews that were analyzed using the deep hermeneutic method and grounded theory, four types of care orientations were identified. We find that care plays a significant role in boys’ lives, whereby the degrees of caring attitudes and practices as well as the specific connections between care and masculinity vary significantly. The article shows that pronounced care orientations are not necessarily accompanied by a rejection of traditional norms of masculinity and domination, as some scholars on caring masculinities suggest. We therefore argue for an open-minded approach to analyzing the ambivalent relation between care and masculinity.