This study reports on a survey of 166 gay men in Sydney, Australia, that explores the links between internalized shame, internalized homophobia, and attachment style. These variables were linked to the age of coming out, family and peer acceptance of their sexuality, relationship status, and previous marriage. Findings suggest a strong relationship between shame, internalized homophobia, and anxious and avoidant attachment style. Shame was predicted by internalized homophobia and anxious and avoidant attachment style. A significant proportion of gay men reported that they were not easily accepted when they first came out. There was a significant relationship between coming out and internalized homophobia but not with shame and attachment style. Furthermore, men who had never come out to family and friends reported higher levels of internalized homophobia but not higher levels of shame and attachment style. Of particular significance was the connection between previous marriage and higher levels of shame and internalized homophobia. Finally, gay men who were not currently in a relationship reported higher levels of shame anxious and avoidant attachment style. These findings are related to therapeutic work with gay men who have previously been married and those who are concerned with their current single status.