Experiments 1 and 2 examined whether winning versus losing led to reckless betting for real prize money. Experiment 2 also assessed whether positive or negative emotions were linked to such reckless betting. College students were randomly assigned to experience primarily either wins or losses during the rigged first round of a computerized card tournament that had 2 independent rounds. For the second round, participants' chip totals were reset and cards were dealt randomly. In Experiment 1 (N = 107), participants in the Initial-Winning, as compared with the Initial-Losing, condition bet more recklessly (i.e., bet too many chips when a loss was likely). Experiment 2 (N = 72) again showed that Initial-Winning participants bet significantly more recklessly than did Initial-Losing participants. It also revealed that positive affect was significantly positively correlated with such reckless betting. These findings have implications for understanding how college students, those at an age when they are especially vulnerable to problem gambling, can come to lose more money than they can afford. Initially winning and positive affect when gambling could be risk factors.