The authors' previous work with long-term family caregivers demonstrated the importance of conversational cues, the reliance on humor to convey sensitive information, and the ways in which the interviewer can follow up, with appropriate probes and nonverbal encouragement, to gain necessary insight into the caregiver situation. This article offers specific suggestions for achieving more productive and satisfying interviews with family caregivers who rely on humor to help them tell their stories. Bateson (1972) was one of the first theorists to note that communication involves more than simple message translation. The interviewer and interviewee communicate with each other and also communicate about the communication. Each interactant in a conversation plants cues (humorous anecdotes, for example) to suggest how a message should be handled. Long-term family caregivers are frequently asked to talk about topics such as bowel movements, loneliness, personal safety, and intimate care. Social workers, physicians, nurses, and other health and human services providers conduct numerous interviews and historical accounts of their patients' lives, yet often fail to probe for deeper and richer information that may be just beyond the typical interview exchange. Several researchers have documented the problems that patients have in trying to express their emotions to their doctors. There is strong evidence that those who conduct interviews with family caregivers must be taught to recognize the problems and issues embedded in interview data and concealed by humorous communicative cues and anecdotes. Effective interview probes in situations where humor has been introduced are different from those used for other communication exchanges. Among other things, the interviewee may not be conscious of his or her effort to convey important information through humor. For some, the disguise of humor may also be serving as a protective shield in the communication exchange. Savvy health and human services providers and researchers know how complex and challenging it can be to obtain complete and accurate information from individuals who have much information to share and many emotional barriers to overcome in a communication process.