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Research on advertising containing negative information, such as two‐sided messages, has neglected the potential of including humor in the advertisements, although both theory and practical examples suggest that humor might help to sell negative information. This paper presents the results from three studies that showed that humor can increase the persuasive influence of two‐sided advertising due to a positive surprise effect. However, it can also reduce this effect for high‐involvement consumers due to a negative distraction effect. Because two‐sided advertising is particularly effective in targeting high‐involvement consumers, this study established humor–product fit as a boundary condition to help mitigate the negative effects on high‐involvement consumers who are exposed to two‐sided advertising messages. When the fit between product and humor is high, the persuasiveness of two‐sided advertising for high‐involvement consumers increases. The study's findings have implications for theory and for the practice of including negative information in advertising. Humor can be applied in two‐sided advertising if consumers are highly involved and the humor is appropriate to the product.