Hemophilia is a congenital bleeding disorder that predominantly affects men. Home intravenous replacement of missing clotting factor is the most effective treatment; however, the uptake of preventative treatment (also known as prophylaxis) varies among men with hemophilia. The purpose of the current qualitative study was to describe the connections between masculinities and men’s (n = 11) experiences of hemophilia across varying age groups. The inductively derived findings revealed bleed-related joint pain as the primary prompt for men to treat or seek medical help. Many men reported experiencing a high number of bleed-related injuries in adolescence, particularly in high school, oftentimes as a result of engaging in idealized masculine physical activities. Though the limitations imposed by hemophilia were contested by most men early on in their lives, as men grow older more conservative approaches were employed both in terms of treatment and activity to reduce the potential for residual bleed-related disabilities. Overall, the results indicate that men with hemophilia may benefit from peer and professional education about recognition, prevention, and optimal treatment of bleeds. Furthermore, masculine ideals act as important context in which men navigate hemophilia management practices and may facilitate contesting or conceding behaviors. Masculine ideals of strength and control may be garnered to facilitate optimal hemophilia management practices.