The first goal of this research was to refine our concept of sense of humor as a multidimensional construct with both positive and negative characteristics. To this end, 166 participants completed the Coping Humor Scale, the Situational Humor Response Questionnaire, the Multidimensional Sense of Humor Scale, and a variant of the Humorous Behavior Q-Sort Deck. Results indicated the clear existence of a higher-order underlying positive sense of humor dimension relating to the socially skilled and adept use of humor. Also indicated were two higher-order negative dimensions. Bawdy humor encompassed both an appreciation of boorish humor and an aggressive use of humor, whereas belabored humor reflected a strained and incompetent use of humor to gain the approval of others. The second goal of this research was to then consider these three higher-order sense of humor dimensions with respect to the prominent personality themes of individualism (e.g., agency) and relatedness (e.g., communion). Participants completed a number of measures assessing these two themes, with our findings indicating that relatedness and individualism both have separate positive and negative elements. The primary sense of humor dimension, socially skilled and adept humor, was broad based, as it demonstrated significant relationships with both positive relatedness and positive individualism. Bawdy humor, in contrast, was much more specific, showing associations only with negative individualism (e.g., autonomy). The other remaining higher-order negative humor dimension, belabored humor, was primarily linked with negative relatedness (e.g., sociotropy), but did show some limited associations with negative individualism. These findings were then considered in terms of multidimensional approaches to sense of humor, individualism and relatedness themes, and various applied considerations stemming from this work.