Whether playing video games with prosocial content has an influence on empathy among players remains contentious in the research literature. Some evidence suggests playing cooperatively with other gamers enhances empathy, but data have not conclusively linked prosocial content with empathy. Further, mechanisms of this potential relationship are unclear, and little work has been conducted on how cognitive skills, such as fluid reasoning, may mediate this relationship. The current study examines these relationships with a large sample of 3034 youth (27.2% female, Mage = 11.2; range 8–17 at time 1) in Singapore. Data were considered longitudinally across two years in three waves. Ultimately, no evidence emerged that prosocial content in video games had any impact on empathy related outcomes, nor was fluid reasoning a mediator variable for any relationship. However, variables such as social competence and depression and anxiety symptoms were highly related to empathy measures. This evidence adds to the growing debate in the field that video games may not dramatically alter, whether positively or negatively, the development of emotional and behavioral outcomes for youth.