People use social media to achieve particular gratifications despite expressing concerns about the related privacy risks that may lead to negative consequences. This inconsistency between privacy concerns and actual behaviour has been referred to as the privacy paradox. Although several possible explanations for this phenomenon have been provided over the years, they each consider only some of the obstacles that stand in the way of informed and rational privacy decisions, and they usually assume a static situation, thus neglecting the changes taking place over time. To overcome these limitations, this article incorporates all the key privacy obstacles into a qualitative system dynamics model and examines the conditions under which the privacy paradox emerges over time in the context of social media. The results show that the privacy obstacles prevent adequately accounting for the negative consequences by (1) reinforcing gratifications, thus inducing social media adoption and use, while (2) hampering the realisation of (all) negative consequences, thus reducing the motivation for social media discard. Moreover, gratifications kick off early and often seem to dominate even major long-term negative consequences, thereby resulting in users becoming only gradually concerned about privacy, by which time they are usually deeply engaged in the platform to consider discarding, and therefore arriving in a paradoxical situation that seems not viable to escape from (i.e., the boiling frog syndrome). Conversely, major short-term negative consequences are more likely to conflict with gratifications already earlier, thereby resulting in users becoming less engaged, more concerned, and therefore still able to discard the platform, thus resolving the paradoxical situation.