Retargeted advertising allows businesses to deliver relevant information to targeted audiences using individual level data, resulting in enhanced advertising effect and optimized return on investment. This research investigates the level of targeting from two distinct viewpoints: product-category-oriented retargeting and product-character-oriented retargeting. To uncover the underlying mechanism of users’ reactance to retargeted advertising, this research develops a model to predict consumers’ click-through intention. I consider two new aspects-perceived seductiveness and perceived serendipity-to seek a deep understanding of Internet users’ perception on retargeted advertising. In addition, this study tries to find out how a match or mismatch between users’ goals concreteness and the concreteness of retargeted advertising influences the advertisement effectiveness.