This explorative study aimed to develop an understanding of how a sample of two groups of men, considered to be situated at different ends of Connell’s masculinity continuum, construct their masculinity, and how these constructions relate to their proximity to violence against women (VAW). One group consisted of five men incarcerated for violent crimes (MIVC) that had previously used VAW. The other included five participants in the pro-feminist group Men Against Violence (MAV), without prior VAW. An abductive approach, using qualitative interviews, was employed. Results show that the MIVC participants appeared ambivalent, unreflective, and inconsistent in their masculinity constructions, and used VAW as part of their problem-solving repertoire. The MAV participants appeared to have a reflexive stance towards gender equality and consistently adopted inclusive ways of enacting masculinity and preventing VAW. The study can only provide some support to the postulated relationship between men’s masculinity positions and their attitudes toward VAW.