This chapter takes as its starting point a comparison of the trajectories of two women from different generations and different ethnic and religious backgrounds. Both were to a considerable degree ‘self-made’ women, and one question raised by their narratives is how is marriage relevant to their success? The stories that these women tell are replete with ethical judgements and reflections on their own and their parents’ marriages as well as those about others. The apparently tangential significance of marriage in these stories is suggestive. Seemingly, a necessary part of a normative life course even in an unconventional scenario, marriage here takes forms that are at once accepted and also ‘transgressive’. Both women had married foreign husbands; in one case, this ended in divorce; in the other, what seemed a successful partnership endured. We see how marriage allows the expansion of convention but, paradoxically, also reinforces social norms. Indeed, at the boundaries of difference and what is acceptable, marriage has the capacity to be re-enfolded into what is normative through its conventionality. In this way, it holds a promise of transformation for individuals and families, and for wider communities and nations.