Close relationships between men and women have been theorized from feminist, psychoanalytic, and political economic perspectives. In seduction communities, dating coaches and pickup artists act as expert mediums in scripting norms of heterosexual courtship between men and women. Based on an ethnographic analysis of intimate labor between coaches and male clients in seduction communities based in New York City, this article suggests three things. First, that apprenticing in techniques of heterosexual seduction is about masculine self-fashioning; second, that men experience culturally-based ambivalences around norms of self-help—including ideas of freedom, dependency, and addiction—in ways that fashion their bodies, speech acts, and identities as objects of desire for women; and third, that practices of seduction complicate heteronormative masculine identities by creating intimate spheres of dependency and self-disclosure among men. This article follows men’s trajectories of learning seduction skills, and finds that men rely on competing rhetorics of authentic expression and technical self-presentation that seek to manage (in ways that also reproduce) a range of social, economic, and gender-based inequalities.