Parenthood is a significant life transition with considerable impacts on parent, child and family wellbeing. While life-enhancing, it is also stressful. New parents’ often hold unrealistic expectations and do not prepare adequately for the new role. Applying a critical exploratory Grounded Theory approach, this study explores the reasons for expectant parents’ unrealistic expectations. Thirty parents were interviewed about their preconceptions of parenthood, how they impacted on early parenting experiences and what, if anything, might help better prepare parents for this role. Participants reported unrealistic expectations, a lack of preparation, and recommended that parenting information be provided by professionals prenatally to help prevent adverse effects. In addition, we advocate promoting critical thinking to help parents identify and grapple with facets of social life that support and impede the way they experience and cope with parenthood, leading to the capacity to challenge cultural pressures that may make parenting even more difficult.