The ‘intimate horizons’ of algorithmic, self-tracking technologies have become increasingly important. These applications are no longer perceived as distant, instrumental entities, but offer a more affective and intimate experience. In this paper, we address the long-term experience of living with a digital contraception technology that utilizes self-tracking. We draw upon four design workshops with a total of 14 users of the app Natural Cycles to illustrate moments of ambivalent affects and oscillating relations. Based on our analysis, we concretize four dimensions of ambivalence in different scales and temporalities. We propose three strategies of designing with these unavoidable disruptions, conflicting feelings, and shifting relations to acknowledge users’ agentic engagements, nuanced dynamics of intimate self-tracking experiences, and users as embodied and affective beings. We contend that by attending to these existential ambivalences, digital contraceptive can become better configured to plural modes of life and long-term intimate relations that they engender.