Distress disclosure has been linked with reduced psychological distress, increased wellbeing, and successful psychotherapeutic outcome. Because of the importance of distress disclosure, researchers have worked to develop and improve theoretical models of disclosure to facilitate counseling practices that reduce impediments to disclosure. Presently, we conducted a 2-part study to investigate distress disclosure’s associations with attachment avoidance, gender, and alexithymia—3 constructs frequently linked with disclosure. In Part 1, we examined the extent to which attachment avoidance, alexithymia, and gender predicted general disclosure tendencies. In Part 2, we examined the extent to which attachment avoidance, alexithymia, and gender predicted event-specific disclosure. Participants were recruited from a crowdsourcing website (N = 178 in Part 1; N = 108 in Part 2). In Part 1, alexithymia partially mediated the association between attachment avoidance and disclosure tendencies, and the link between attachment avoidance and alexithymia was stronger for men than women. In Part 2, the association between distress intensity and event-specific disclosure was weaker for people with high levels of alexithymia. Implications for counseling theory and practice are discussed.