The purpose of this study is to search for any difference in self-expression of Second Life residents with different levels of shyness. For this purpose, we used sixty students from two fifth-grade elementary school classes. Thirty students were assigned to the high shyness group and the rest to the low shyness group. Each group completed pre- and post- self-expression tests. After six weeks of speaking activities in Second Life, the results indicate that self-expression scores increased for students in both the high and the low shyness groups. The low shyness group showed an increase by 1.00 in the self-expression score. However, the high shyness group showed an increase by 3.14 after the speaking activities. This result suggests that Second Life can be a good environment to enhance self-expression in students, especially those with degrees of high shyness.