Although many individuals are searching for love, failure can often be the expected outcome. A previous study investigated self-sabotage in romantic relationships and explored how psychologists in practice understand this phenomenon. A repertoire of self-sabotaging behaviors was identified by practitioners, with possible reasons as to why this occurs. The present study was the first to empirically explore self-sabotage in romantic relationships by gathering qualitative evidence from a diverse sample of 696 individuals. Participants’ lived experiences detailed motivations and strategies to self-sabotage romantic engagements. However, participants’ experiences have also helped inform essential steps toward breaking the cycle of self-sabotage.