The limited number of studies on intergenerational play suggests that not many parents play video games with their children (Lenhart, Jones, & Macgill, 2008). However, when intentionally designed to support intergenerational play, video game could provide an opportunity for parents and children to connect in new and powerful ways, especially around adolescence--a time when family relations undergo major transformation. Using the lens of socio-cultural theoretical framework and activity theory, this dissertation investigates how to design educational video games to support intergenerational play where parents and children spend quality time together while engaging in collaborative work. Sixteen mother-child dyads (children ages 10 to 13) were observed while playing different game scenarios designed around dilemma situations and personally relevant issues in the context of Family Quest--a family game space created within Quest Atlantis, a three-dimensional educational gaming environment (www.QuestAtlantis.Org). The findings suggest that games designed around both dilemma situations and personally meaningful issues created conversations between mothers and children, and provided an opportunity for mothers to spend one-on-one time with their children. Mothers gave more directives to their children when playing through game scenarios that lacked dilemma than those that were designed around a dilemma situation. In addition, gender differences were found in mother assistance behaviors, e.g. mother gave more directives to their daughters than their sons. Collaborative discussions were observed only in the game scenario that involved a dilemma around an issue that was removed from family daily life. During follow-up interviews, mothers who had no previous experiences playing video games with their children reported enjoying the experience, and expressed an interest in continuing to play Family Quest with their children in the future. The analysis of different cases of mother-child dyads suggest that mothers and children who worked as equal partners were also the ones who engaged in collaborative discussions and family conversations around real world experiences during their gameplay. Together, these findings illuminate the value and design principles of designing educational video games to support intergenerational play, and outline the direction of future research. [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.]