Prospective gay fathers must carefully prepare, plan, and think about parenting—often for years—before they become parents. This article explores how different paths to parenthood provide opportunities for Canadian gay men to reflect upon their preferences for surrogacy or adoption, the meaning of fatherhood in the absence of a woman as a primary caregiver, and the opportunities and potential shortcomings of gay fatherhood. Based on analysis of 23 in-depth, semi-structured interviews with Canadian prospective gay fathers, I show that adoption and surrogacy foster different degrees of reflection along the journey to fatherhood. I argue that gay men who pursue surrogacy express masculine competence and draw upon scripts of conventional fatherhood, while gay men who pursue adoption experience a disruption in their masculine competence and must reflect on their potential inadequacies as male parents. Further, I include a brief discussion of some counterevidence: these pressures on the journey to gay fatherhood can be resisted through a queer, anti-racist, and feminist consciousness.