Communication between parents and adolescents about sexuality faces challenges due in part to sociocultural factors. This study aimed to document the attitudes of parents and adolescents about communication regarding sexuality. The results emanate from the baseline measurement of the Cuídalos Project. The presented data is part of a larger study that aimed to evaluate a web-based module to foster communications between parents and adolescents (13-17 years of age) on health-related issues. In this article, we present the baseline data in which participants answered questions on their comfort when talking about sexual health issues. The sample was composed of 458 parent/adolescent dyads (n=916). We carried out a frequency and central tendency analysis of the gathered data. The average age for adolescents was 15 years of age, and 15% were sexually active. Adolescents reported better attitudes towards sexual communication than parents. Still, parents understood that they shared sufficient information on sexuality related topics. Parents and adolescents reported some level of difficulty and lack of comfort when talking about specific prevention methods. Results highlight the need to incorporate parents into interventions geared for adolescents and their sexual health. In Puerto Rico, it is necessary to develop programs that aim to reduce high-risk sexual activity among adolescents.