The purpose of this paper was to examine the relationships of homosexual male students at the senior high school level and their loneliness using parental bonding attitude as a moderating factor. An amount of 127 homosexual male senior high school students in Taiwan is studied. The Pearson correlation analysis and the hierarchical regression analysis are adapted to examine two proposed hypotheses. Based on the results, homosexual male senior high school students in both hyper-masculine and feminine gender roles are found to feel loneliness, but levels of loneliness of those who possess hyper-masculine gender role are relatively lower than those in a feminine role. In addition, the levels of loneliness of homosexual male senior high school students could be negatively affected by parental bonding attitudes (Care). Recommendations and suggestions for parents as well as teachers of homosexual senior high school male students and future studies are underscored at the end of this article.