Humor can be an effective means for introducing or modulating a discussion on matters of personal importance. This paper examines the circumstances under which humor appears in conversational self-disclosures with friends. In an exploratory sample of 94 cases of self-disclosing humor from natural peer conversations, the study found humorous self-disclosures and self-disclosures accompanied by laughter to occur in the continuation of an ongoing topic within the contexts of humorous rounds, troubles talk, complex narration, and entertainments. It also found humorous self-disclosures to be involved in topic changes within conversation and as reactions to accidents and teasing. Extensive examples of each type of humorous self-disclosure are provided and these illustrations are discussed in light of prior research on gender differences.