ABSTRACT Despite increasing engagement with mental health services in Australia, therapy dropout rates for men remain high, most commonly due to a lack of connection with their therapist. Previous studies have examined the challenges men face when attending therapy, the obstacles therapists encounter when working with male clients, and the subsequent recommendations for therapist training that have emerged from these findings. However, to date there has been no investigation into the experiences and needs of trainee therapists working with men. It is unclear how their status as trainees influences their perception and adaptability when providing care for male clients. The current study therefore explored psychology trainees’ expectations, experiences, and preparedness regarding their psychotherapeutic work with men. Qualitative interviews were conducted with 12 students undertaking clinical psychology training from a single Australian University, focusing on their experiences working with male clients throughout their clinical training. Reflexive thematic analysis was undertaken to develop three themes: (1) Mismatched expectations of manspeak, which explored the ways in which students expected and experienced male engagement, (2) Gratifying work, which highlighted elements of therapeutic work with men that shaped participants’ sense of competence, and (3) Working with the “macho man”, which described the challenges of working with men, such as managing boundaries, misogyny, and personal safety. Findings suggest psychology trainees may benefit from additional training in university curriculums which specifically addresses some of the complexities of therapy with men. This training could illuminate how masculine socialisation affects men’s engagement in psychotherapy in practice and provide strategies for trainee therapists to support male engagement.