In contemporary Japan, an ever-increasing number of anime (animated films) incorporate real-life scenery into their background imagery. Fans intent on making a connection with their favorite anime characters often decide to visit the depicted places. They commonly refer to this activity as a ‘sacred-site pilgrimage’ (seichi junrei). Over the course of several years beginning in 2007, I have researched the pilgrimage related to the anime production titled Higurashi no naku koro ni (overseas release name: When They Cry). In particular, I have documented how fans illustrate prayer tablets (ema) with anime characters that they then display at a Shinto shrine as part of their pilgrimage. On the tablets, many fans write prayers and messages, sharing their thoughts and feelings about the anime characters, the pilgrimage, the fan community, and life in general. Interestingly, however, the fans, who are mostly in their teens and early 20s, inject emoticons, specifically kaomoji, into the text of their prayers and messages. Of course, this is reflective of their generation’s ‘fluency’ in terms of digital communication. Looking closely, however, we can also observe that fans use kaomoji in creative and artistic ways. In fact, fans have created new expressions with kaomoji based on the speech of Higurashi no naku koro ni characters and have even adapted kaomoji into the character illustrations. In this chapter, I examine the use of emoticons on prayer tablets, taking note of changes over time, in order to evaluate the significance of this digital-to-analog transference.