This study investigates a type of online language play popularized on the Taiwan-based Internet, including the rendering in Chinese characters of the sounds of Taiwanese and Taiwan Guoyu (Taiwanese-accented Mandarin), which are defined as Stylized Taiwanese and Stylized Taiwanese-accented Mandarin, respectively. The playfulness inherent in these stylized practices has multiple sources. First, they manipulate the Chinese writing system and create an incongruity between sound and meaning. Second, they call attention simultaneously to a number of functions of language (Jakobson, 1960). Third, the two stylized practices bring into play the respective social meanings and stereotypes associated with their spoken counterparts. Thus the superficially similar forms of language play may be interpreted differently and further serve subtly different interactional functions in face-threatening situations. Two cases of stylized practices are examined in detail to illustrate how stylized language play is used to mitigate potential tension, to show positive affect, and to regulate appropriate group behaviors simultaneously.