Divorce is considered distressing for many individuals (Sbarra et al., Current Directions in Psychological Science, 2015, 24, 109); however, individuals in poor‐quality relationships may experience certain benefits of leaving an unstable union (Amato & Hohmann‐Marriott, Journal of Marriage and Family, 2007, 69, 621). On–off relationship cycling, or the breakup and reconciliation of a relationship, is a salient indicator of poor relationship quality and a common form of relationship instability (Dailey et al., Personal Relationships, 2009, 16, 23) that is associated with distress (Monk et al., Family Relations, 2018, 67, 523). In line with divorce–stress–adjustment and relational turbulence theory perspectives, we hypothesized that those whose relationships were characterized by on–off instability would experience less distress during the separation and divorce process. Given gender inequality in marriage (e.g., Dempsey, Journal of Sociology, 2002, 38, 91; Monin & Clark, Sex Roles, 2011, 65, 320), we also hypothesized that this association would be more pronounced for women. Using data from 98 divorced or separating couples, we found that relationship cycling prior to the separation and divorce process was associated with fewer distress symptoms for women. Conversely, a history of relationship cycling was associated with more distress symptoms for men. Our study provides support and extends prior investigations illustrating that, for some, those in unions characterized by more turmoil, may experience relief following a termination.