In the advertising research literature, polysemy is defined as different interpretations for the same advertising message. The multiple ad-interpretations can be attributable to complexities and diversities in culture and/or consumers’ own demographics, perceptions, attitudes, lifestyles, values, behavior, and psychographics. We provide a bipolar and dichotomous perspective on advertising polysemy as positive and negative polysemy with research and practice examples from the print advertisements for alcoholic beverages and corporate social responsibility to explain the conditions that lead to the emergence of positive and negative polysemic contexts for the same message. Furthermore, the study explores how polysemy leads to better branding. The research investigates the concept of polysemy and the generation of idiosyncratic meanings, and examines the impact of advertising polysemy on consumer-based brand equity. The research proposes and measures the advertising polysemy and consumer-based brand equity conceptual framework supported by accommodation theory, consumer response theory, and theory of hierarchy of effects, leading to stronger ad-evoked feelings, ad and brand attitudes, and consumer-based brand equity.