This article builds on an earlier piece in this journal (Power, 2018) which hypothesised about the differences between three routes into relationship: random romance, arranged marriage, and self-arranged relationships. Interviews with three couples, one from each tradition, are used to explore how attachment dynamics were creating both a challenge and a resource for each couple. This article uses psychoanalytic thinking to inquire about mate-selection, and then attachment theory and emotionally focused couple therapy (EFT) (Johnson, 2012) to understand how these couples built a long-term attachment bond in each tradition. The couples’ own words are presented with reflections by the author in order to demonstrate challenges that couples face and ways in which they can sometimes manage these.