To an advertiser, personalized advertising means shrinking the purchase decision funnel - delivering relevant content to the right user at the right time. However, personalized advertising is a double-edged sword for consumers. This tension between consumers wanting relevant advertisements yet feeling discomfort when faced with a personalized advertisement that used their data without their consent has been labeled as the personalization privacy paradox (Aguirre, Mahr, Grewal, de Ruyter, & Wetzels, 2015; Awad & Krishnan, 2006). In this scenario, through the privacy calculus lens, consumers behave as if they are performing a risk-benefit analysis in assessing the result of information disclosure (Xu, Luo, Carroll, & Rosson, 2011). This research explored the relationship between advertising personalization and privacy by examining the impact of two previously unconsidered factors influencing the risk-benefit analysis: the consumer-brand relationship between the ad recipient and the brand being advertised and the platform context, Facebook vs. Twitter, wherein the ads are delivered. We found no effects for platform context on the consumer’s perceived benefits and risks of information disclosure. We also found that when strong brand relationships are present, if perceived benefit is high, then perceived risk minimally alters the consumer’s perceived value. Furthermore, with weaker brand relationships, perceived risk has a stronger effect on perceived value even when the perceived benefit is high.