Research has suggested that regulatory fit creates value. In this study, the regulatory fit was defined as the fit between the regulatory focus and the advertising messages. We investigated the effects of regulatory fit on the evaluation of messages when familiarity with the message was low. This hypothesis was supported by two observations; when the familiarity with a message was low, regulatory fit was not observed among participants with a prevention focus. In contrast, regulatory fit was observed among participants with a promotion focus, with a higher preference for two-sided advertising. The significance of familiarity on the effects of regulatory fit and value is discussed.