Men's engagement in parenting programmes can positively impact them and improve their children's life outcomes. However, men are underrepresented in parenting interventions, including the Theraplay parenting workshop (TPW) delivered at Stand in Aotearoa, New Zealand. This study examined the effectiveness of the Therapy parent workshops for fathers and male caregivers in Christchurch to evaluate if it met their needs. In this qualitative research, fathers and male caregivers were interviewed to understand their experiences and address the potential barriers to engagement. The analysis indicates that several factors influenced their engagement, such as the influence of professional support people, agencies understanding and targeting their needs, support with accessibility, and the men’s motivations to want to improve their relationships with their children. The identified barriers were the influences of others, such as professionals and other caregivers, societal expectations regarding their role as fathers, a lack of information, and accessibility. The findings suggest that a targeted approach is needed by service and education providers that meet the needs of fathers and male caregivers to increase their engagement in parenting interventions, and at present, this is lacking.