Although many practitioners have turned to the Internet as a viable means of reaching youth with their programs, there is little research on how and when youth engage with online educational resources. The present study employed a grounded theory design to gain an understanding of how practitioners can develop online programs that engage youth. Participants completed face-to-face interviews (n = 27) and reviewed two online programs that addressed relationship education (n = 22), which provided the foundation for the analysis of how youth's preferences for online program characteristics are linked to their online program exposure and ongoing participation. The analysis resulted in a four stage model of engaging youth in online programs, with a focus on the types of content, or topics (i.e., work/careers, social skills), technological tools (i.e., social networking platforms, videos), and delivery style (i.e., entertaining, opportunities to give/receive feedback) preferred by older adolescents. Implications center on the types of content (e.g., work/careers, social skills, relationships, media literacy) and delivery modes (e.g., the different instructional pathways for the various topics covered) that practitioners should consider. Additionally, future research that quantitatively examines the four-stage model and individuality among youth, or qualitatively allows youth to be a part of the program development and evaluation process is discussed. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]