What happens when a qualitative/theoretical scholar of gender/sexuality and cultural studies and a quantitative behavioral scientist step outside the boundaries of our respective disciplines, risking disruptions to our normal procedures and cherished political and theoretical commitments? Our unlikely collaboration allowed each of us to explore and challenge the possibilities, limitations, and consequences of our approaches to the study of gender and finance and, ultimately, to make new knowledge. The occasion for this collaboration is the Arizona Pathways to Life Success (APLUS) study, a longitudinal study of a group of young adults to understand how financial practices develop and the factors that shape those practices. We begin by presenting our respective research agendas and our concerns about “engaging the opposition.” We then narrate the sequence of our efforts: to talk and think together, generate analyses and interpretations, and then interrupt ourselves—only to begin again. Ultimately, despite (or perhaps because of) our divergent backgrounds, our final set of findings, which reveals the changeability of participation in gendered constellations of financial attitudes and behaviors over time, challenges dominant scientific and popular understandings of the relation of gender to financial behavior and attitudes, with implications across many domains of research, policy, and educational practice.