In a world where opportunities and chances are common, the phenomenon referred to as “generation maybe” describes people in their 20s and early 30s who are usually being indecisive. With the increase in breadth of information and choices, the number of people who are hesitant in deciding whether to purchase increases at a fast pace, as does the number of products and services targeting this group. In order to enhance our understanding of the phenomenon of consumer hesitation, this study explores contextual factors and consumer characteristics that affect consumer hesitation in the purchase decision-making process. Specifically, this study examines whether seven contextual factors, self-determination tendencies, and five decision-making styles influence consumer hesitation in the product decision making process. An online survey was administered to test our research questions. A total of 309 Korean consumers (female= 48.9%) aged from 20 to 35 were surveyed. A regression analysis revealed that four contextual factors (product involvement, need for information on alternatives, relative price, and uncertain need), two sub-dimensions of self-determination (perceived competence and relatedness), and two decision-making styles (price seeking and advice seeking) have noticeable influences on consumer hesitation. We also found that the degree of consumer hesitation positively influences consumer post-purchase satisfaction. The study concludes with discussions and practical implications.