In a behavioral observation study with dating couples, we examined (a) how attachment orientations predict humor use and (b) how people respond to their partners’ use of humor. Couples were videotaped while trying to resolve a relationship conflict. Each discussion was rated on several theoretically relevant dimensions. Highly avoidant individuals used more aggressive humor and less affiliative humor during their discussions, whereas highly anxious individuals used more self-defeating humor. Individuals also tailored their humor use to partners who were highly anxious and distressed. Aggressive humor was received more negatively by partners who sought more care. Affiliative humor was favorably received, especially when partners were more distressed, whereas self-defeating humor elicited negative responses from highly distressed partners. Both highly anxious and avoidant individuals reacted unfavorably when they were the recipients of the humor styles they used most often. The implications of these results for our understanding of relationships and humor are discussed.