Purpose: The purpose of this study was to explore caregivers' comfort levels and preferences for answering sensitive questions about themselves and their children in a pediatric dental setting. Methods: An electronically delivered survey was completed by 206 caregivers in the waiting area of a dental school's pediatric clinic. The survey items assessed were demographic, general health, behavioral health, oral health, and living conditions. A factor analysis was conducted for each set of questions, and a mean comfort level was calculated for each factor. Comfort levels were assessed on a five-point Likert scale, with one being least comfortable and five being most comfortable. Results: The questions caregivers were less comfortable answering about themselves were concerning traumatic events, stress, coping (mean equals 3.39), and living conditions (mean equals 3.24) versus demographics (mean equals 3.84) and physical and oral health (mean equals 3.99; P<0.001). They were also less comfortable answering questions about their children's trauma, stress, coping (mean equals 3.65), and experiences with violence and sexual activity (mean equals 3.13) than about demographics/general health (mean equals 4.11) and oral health (mean equals 4.21; P<0.001). The main reasons for the discomfort were the questions' sensitive nature and their belief that they had any relationship to their children's oral health. Conclusion: This study provides knowledge of caregivers' lower comfort levels discussing sensitive topics in a dental setting and provides context for interventions focused on how dentists can better communicate with caregivers about their own adverse experiences as well as their children's.