Targeting the most valuable users and generating advertisement clicks from them is a veritable challenge for online advertisers. Most of the extant research about behavioral targeted advertising focuses on matching advertisements with the right people by profiling users’ latent interests. This study posits that users’ individual browsing situations should also be examined with relation to the advertisement clicks. We introduce a new angle—browsing situation routineness—to explore the impact of browsing situations on users’ advertisement clicks. Supported by a unique clickstream data set, our empirical study indicates that consumers are more likely to click the advertisements when they visit websites with high content routineness (CR), particularly in leisure-oriented websites. However, time routineness (TR) works in the opposite manner; users tend to click fewer advertisements during their routine browsing time, compared to non-routine browsing times. We also find that CR and TR have a complementary joint effect to increase click-through rate. The present study contributes an alternative dimension—targeted advertising based on individual browsing situation routineness—to research and practices about behavioral targeted advertising.