During the last decades, new forms of men’s rights activism have emerged, commonly referred to as the ‘manosphere’. This loosely connected, misogynistic online movement particularly attracts young men. Its shared ideology is the Red Pill, a neoconservative ideology that adopts essentialist notions of gender and sexuality, and selectively employs evolutionary psychology to support male supremacy. While the discourses of the manosphere have been mapped, little research exists on how and why young men join and leave such misogynist groups. This article contributes to critical youth and feminist scholarship by analysing the gendered dynamics of online misogynist radicalization pathways. Based on narratives shared on a Reddit community for former ‘redpillers’, this article explores 30 young men’s experiences of entering and exiting the manosphere and details the essential role of vulnerability in these processes. The stories are synthesized into three phases to illustrate the paths in and out of the manosphere.