This study proposed that men are more likely to take greater risk after a win ('house money' effect), while women are more likely to take greater risk after a loss (escalation of commitment effect). These effects are, however, moderated by prior experiences in risk-taking and role characteristics. Three distinct groups of 30 subjects (total = 90) each were solicited to play an experimental betting game. The subjects were categorized into risk providers (RP), risk customers (RC), and non-risk customers (NRC). RP are represented by casino executives, RC by leisure life-time casino gamblers, and NRC by non-casino gamblers. On average, RC group was found to take most betting risk. Male RCs were more likely to bet more after a win, while female RCs were more likely to bet more after a loss. NRCs, irrespective of gender, were more likely to bet more after a loss. There were no gender risk-taking differences in prior outcomes in the RP group.