- Urban African American adolescents exhibit high levels of risk behavior, disproportionately high rates of sexually transmitted infections (STIs), and are at risk for acquiring Human Immunodefiency Virus (HIV). To date, interventions that address the high rates of STIs in this population demonstrate only moderate efficacy. As researchers strive to develop more effective interventions, social-ecological factors and developmental and gender issues are being considered. This study aimed to provide insight into the gendered characteristics of heterosexual urban African American adolescents' romantic relationships, and how these characteristics impact condom use. From a developmental standpoint, sexuality and romance are a normal part of adolescence. Thus, STI/HIV prevention targeted at urban African American youth can be improved if it considers romantic relationship dynamics, and how they influence sexual health behaviors including condom use. To this end, the current study examined the interconnection among interpersonal relationship factors including monogamy, commitment, trust, and respect, as well as intrapersonal relationship factors including gender and relationship history. Furthermore, this study examined how these inter- and intrapersonal factors impact youths' condom use behaviors. This research was guided by the existing literature, theoretical frameworks (i.e., the ecological perspective on health, Rusbult and Buunk's commitment theory, and Rotenberg and colleagues' trust framework), and the "directed perspective" (i.e., lens theory). A qualitative methodological approach was employed to collect data from 52 heterosexual, sexually experienced, African American adolescents (20 females; 32 males) ranging from 15-17 years in age at the time of enrollment. These youth resided in low-income neighborhoods of two large cities in the United States. Data from semi-structured interviews were analyzed using a phenomenological approach. Data analysis took place in four primary stages including: (a) development of case summaries; (b) development and refinement of codes and a codebook, and organization of data using matrices; (c) content analysis and reliability checks; and (d) reviews and critiques by, and discussions with, other research team members. Numerous themes and subthemes that provide insight into the multifaceted characteristics of urban African American adolescents' romantic relationships emerged. Findings show that study participants' romantic relationships were indeed characterized by gender-specific beliefs and behaviors, but that some beliefs and behaviors were similar across gender. For instance, males and females alike acknowledged positive feelings towards monogamy, trust, and respect, and they considered these dynamics as closely linked. That is, males and females viewed monogamy as indicative of commitment, and monogamous and committed relationships were those that were trusting and respectful. Youths' relationship experiences, however, contradicted their ideals to a great extent. For instance, despite the finding that males held positive perceptions of monogamy, they often engaged in multiple partnerships. This finding that shows young African American males’ often engage in multiple partnerships corroborates other research. Furthermore, these data provide insight into the social pressures experienced by urban African American males that encourage them to engage in multiple partnerships and remain uncommitted. According to the current findings, males' multiple partnerships set in motion a breakdown in relationship dynamics (i.e., lack of commitment, mistrust, disrespect), and thus youth experienced less-than ideal romantic relationships. Adolescents' less-than ideal experiences subsequently impacted their current and future romantic relationship beliefs and expectations. For instance, because males were frequently non-monogamous, females did not commonly express commitment to or trust in males. Despite this, only a few females talked about breaking up with a partner whom they mistrusted. Males, on the other hand, considered being monogamous and committed when they had negative experiences with being in multiple, uncommitted sexual partnerships. In addition, relationship dynamics, most noticeably trust (although trust was intricately linked to monogamy, commitment, and respect), impacted condom use. Although adolescents considered condom use important, males and females considered not using condoms when they were with a partner whom they trusted was monogamous and free from STIs. Furthermore, some male respondents talked about the need to balance the protection that condoms provided with the pleasure experienced when not using them. With casual and mistrusted partners, safety tended to take precedence; with more serious and trusted partners, pleasure tended to take precedence. Finally, these data elicited gender similarities and differences related to romantic respect perceptions. Across gender, respect was thought to be an important dynamic in romantic relationships, and one closely related to monogamy, commitment, and trust. Because beliefs about respect were interrelated with beliefs about other relationship dynamics that impacted condom use, respect may also impact condom use. The findings of this study suggest that youth have an understanding about how to develop healthy romantic relationships in adolescence and, in turn, healthy romantic relationships in adulthood. That said, respondents had little to no experience with being in healthy relationships. These study findings can help guide future research, and inform sexual health interventions. For example, investigators should explore further males' belief that monogamy is positive, as this belief frequently contradicted their related behavior (i.e., males often had multiple sexual partners). Finally, future interventions, including dyadic-level interventions, should focus on the dynamics of relationships. In doing so, the efficacy of STI/HIV prevention efforts targeted at African American youth may be enhanced.