Currently, research explicitly examining masculinity and internalized homonegativity is sparse, and even sparser studies are those using qualitative methods. To address this, this study aims to explore: how gender norms are constructed and experienced amongst gay men; and how gender and sexual identity are experienced in relation to masculine norms amongst gay men. A sample of 32 self-identified gay men aged 22–72 years (M = 34.34, SD = 12.94) participated in an online semi-structured interview on masculinity and homosexuality. The study used Zoom to facilitate the online interviews as it offered privacy, accessibility, ease of use, and voice recording, among other benefits. Thematic analyses revealed gay men’s understandings of masculinity, femininity, and sources of pressure to conform. Furthermore, gay men emphasize the conflict experienced between heteronormative gender and sexuality norms, which highlights the term homosexual male as an oxymoron.