This essay begins with Hubert Dreyfus’s Kierkegaardian critique of the Internet and then turns to Richard Rorty’s neo-pragmatist response, an unpublished text found in the Richard Rorty Papers. After considering these contrasting perspectives, the author proposes a third view, arguing that a rhetorical pragmatist should borrow from both Dreyfus’s critique and Rorty’s defense. The Internet does enable media users who are unthinkingly complacent in their passionate commitments as well as those who are complacently unthinking in their detached, everyday busyness. But the Internet also provides its own unique opportunities for thinking critically and for challenging complacency. After proposing this more rhetorically pragmatic view, the author discusses Rorty’s published and unpublished comments on Kierkegaard more generally, concluding with Rorty’s comparison of Kierkegaard and William James.