By observing and interviewing an experimental class of senior high school students in Taipei, which had been practiced Learning Community theories in their Chinese class for two years, this study aims to explore how learning was experienced by students and to provide a more in-depth reflection on how Learning Community is practiced under a Taiwanese classroom context. The study reveals feelings of ambivalence; while students were inspired to be self-motivated inquirers, they are worried that the experiment will impede their preparation for the college entrance examination. On the one hand, they are encouraged to learn by exploring, clarifying issues through peer discussions; on the other hand, they have to prepare for college entrance examination in which test-driven curriculum remains intact. Though some positive impacts including the improvement of peer-to-peer relations, the equalization of students’ relationship with their teacher, and a more engaging learning atmosphere in the classroom have been found, experiencing both learner-centered and test-oriented influences at the same time had led these students to self-conflicting struggles and a contradictory learning structure.