HIV-positive men are living long and healthier lives while managing HIV as a chronic illness. Although research has extensively documented the experiences of illness of people living with HIV, dating, marriage, and fatherhood among heterosexual Latino men has not been examined. To address this gap, this study used a qualitative study design to examine patterns and strategies for dating, marriage, and parenthood among 24 HIV-positive heterosexual Puerto Rican men living in Boston. The findings in our study indicate that an HIV diagnosis does not necessarily deter men from having an active sexual life, marrying, or having children. In fact, for some of the men, engaging in these social and life-changing events is part of moving on and normalizing life with HIV; these men planned for, achieved, and interpreted these events in the context of establishing normalcy with HIV. Although the HIV diagnosis discouraged some men from engaging in sexual relations, getting married, or having children, others fulfilled these desires with strategies aimed to reconciling their HIV status in their personal life, including dating or marrying HIV-positive women only. Additional important themes identified in this study include the decision to disclose HIV status to new sexual partners as well as the decision to accept the risk of HIV transmission to a child or partner in order to fulfill desires of fatherhood. Understanding the personal struggles, decision-making patterns, and needs of HIV-positive heterosexual men can aid in designing interventions that support healthy living with HIV.