Guided by relational dialectics theory (RDT), we analyzed 85 first-person testimonials of parental regret written by users of the /r/childfree subreddit. We interrogated how competing discourses animate what it means to be a parent (our semantic object). Contrapuntal analysis revealed dominant and marginalized Discourses of Parenting as Heaven (DPHN) and Parenting as Hell on Earth (DPHL), respectively, as well as a third Discourse of Parenting as (the Only) Choice (DPOC). We identified three kinds of dialogically contractive practices including a new form we call fear of missing out (FOMO), two forms of diachronic separation, four forms of synchronic interplay including a new form we introduce (i.e., allying) that is useful when more than two discourses compete, and one form of dialogic transformation. We argue that FOMO serves as a catalyst for diachronic separation. We offer practical implications for fencesitters (those “on the fence” about having children), counselors, and policymakers.