Problem gambling is a gambling disorder often described as continued gambling in the face of increasing losses. In this article, we explored problem gambling behaviour and its psychological determinants. We considered the assumption of stability in risky preferences, anticipated by both normative and descriptive theories of decision making, as well as recent evidence that risk preferences are in fact ‘constructed on the fly’ during risk elicitation. Accordingly, we argue that problem gambling is a multifaceted disorder, which is ‘fueled on the fly’ by a wide range of contextual and non-contextual influences, including individual differences in personality traits, hormonal and emotional activations. We have proposed that the experience of gambling behaviour in itself is a dynamic experience of events in time series, where gamblers anchor on the most recent event—typically a small loss or rare win. This is a highly adaptive, but erroneous, decision-making mechanism, where anchoring on the most recent event alters the psychological representations of substantial and accumulated loss in the past to a representation of negligible loss. In other words, people feel better while they gamble. We conclude that problem gambling researchers and policy makers will need to employ multifaceted and holistic approaches to understand problem gambling.