Research shows young men engage in more risky health behaviors such as physical altercations, drug use, or binge drinking, compared to their female peers. Scholars tend to argue these risky health behaviors are enactments of gender, as men strive to achieve hegemonic masculinity. This dissertation provides a more nuanced explanation of young men's risky behaviors by taking into account the individual's personal goals of masculinity and whether they view themselves as achieving that desired masculinity. Drawing from 87 interviews with middle school, high school, and college-aged men who participate in either band or baseball, I make three main arguments. First, I argue that attainment of desired masculinity, hegemonic or hybrid, is key to one's positive health behaviors. Young men who fail to reach their goals of masculinity describe risky health behaviors as ways to cope with or "prove" their masculinity. Second, I find that boys and young men negotiate peer pressures to engage in sexual encounters in one of three ways: avoidance by deflecting unwanted attention from peers, acceptance by normalizing this pressure, or outright rejection of this expectation. Third, my analysis demonstrates that boys and young men who cite both men and women as role models (compared to those who cite men only) are more likely to reach their desired masculinity. This research contributes to several areas of sociological scholarship including gender, sexuality, family, and youth studies.