Much research has explored the value of video games for changing inactive lifestyles. The purpose of this study was to examine the effects of personality pairings on enjoyment within two gaming scenarios. It was hypothesized that one would enjoy playing with another possessing a personality type similar to their own. Subjective results showed that matched personality pairings particularly enjoyed playing in a competitive game scenario, males reported more enjoyment in competitive game compared to females, and friends enjoyed playing together more than strangers. Objective measures revealed that a competitive game scenario is more enjoyable than a cooperative game scenario. To maximize enjoyment, recommendations for game design include encouraging social interaction between players and integration of a personality test before or during a multiplayer online game. Future research may evaluate other variables such as culture, and alternative personality pairing possibilities for increasing game enjoyment.