The current research adopts the relational interaction and “multi-masculinities” theoretical perspectives, attempting to explore the construction of masculinities in men’s same-sex friendships. A total of 17 college level educated and above, heterosexual, middle class adult males were interviewed. The results show that as participants growed across different life stages, the construction of their masculinities turned from hegemonic style to a more inclusive and gender equal tendency due to their experiences of gender relationships and observations of gender inequality. Participants who are 30 years old and above tended to show more agency in challenging hegemonic masculinity; however, expressing mutual love to each other remained as a taboo among heterosexual males.