bell hooks has written approvingly of the ‘second phase’ of life as a time, in midlife after divorce and relationship breakdown, when women may move from a place of dependency and intimate inequalities towards stridently asserting their needs and desires. This article interrogates these claims about the ‘second phase’ of life through qualitative empirical study. The article builds on our earlier work critiquing narratives of reclaimed control and self-development in the so-called baby-boom generation, showing how the compounded forces of ageism, sexism, classism, and racism are ever-present in mid- and later life romance. We juxtapose two separate ethnographic studies of middle-aged women’s post-divorce moves towards repartnering, one with middle-class White British women and one with working-class British South Asian women, to break open questions of empowerment in mid-and later life. Narratives and practices of self-discovery and renewed independence were common in both our studies, but the motivations for and consequences of these moves were differentiated by intersecting power relations. Narratives of newfound independence did not translate evenly into intimate lives and dating practices, where respectability remained vital and obdurate. Friendship groups diffused sexual agency and worked to maintain traditional practices of femininity. At this juncture of life many types of complicated and often contradictory femininities were played out, and were refracted through differing generational, diasporic and kin moralities. Empowerment in midlife can be ambivalent, laced with continued vulnerabilites and is implicated in a range of intersectionalities.