This article examines future thinking within the mercantile bourgeoisie of the late sixteenth-century Low Countries. Through letters, it explores the marriage story of Daniel van der Meulen and Hester della Faille, scions of two prominent Antwerp merchant families. Daniel and Hester took their vows in Haarlem during the siege of Antwerp (1584-1585), bringing controversy, uncertainty, and fear into the present timespace. This essay aims to contribute to a better understanding of temporal experiences in the past by showing how rupture affected social expectations and envisioned futures within the mercantile family regime. By analysing futural orientations and future-oriented actions related to the occasion of marriage, this article highlights the role of the future – near and far – in the daily life of historical actors, the ways these people shaped their imagined future, and, of course, for what underlying reasons. I argue that aspects such as lifecycle expectations, patrimonial culture, and opportunities for social mobility played an essential role in choices regarding investments of time. Since decisions on the allocation of time were made by those managing the nuclear family, this essay illustrates how the distribution of power – at the micro level – impacted individual lives and subsequently shared futures.