This study explores the influence of situational context on parent-adolescent communication about sexual and reproductive health (SRH) issues in the urban slums of Ibadan, Nigeria. A qualitative exploratory study was conducted in the Southeast and Northeast LGAs of Ibadan. Eight (8) vignette-based focus group discussions (FGDs) with parents and adolescents of both sexes were conducted in addition to four (4) key informant interviews (KIIs) with community and women's leaders. Interviews were tape-recorded, transcribed, and translated into English. Thematic analysis was adopted using ATLAS Ti 9 software. Findings portray SRH meanings and experiences, intergenerational cultural norms, and expectations for SRH, gender double standards in SRH discussion, streetwise SRH knowledge, and social media exposure as contexts that interfere with parent-adolescent communication on SRH issues. The findings show that despite understanding the need for SRH discussion, parents and adolescents lack effective communication on SRH issues due to the interference of unfiltered streetwise SRH knowledge and social media exposure. Also, SRH conversation between parents and adolescents promotes gender inequalities as different information is passed to adolescent girls and boys. Interventions that take into account situational occurrences must be geared towards enabling parents to give their adolescents early exposure to relevant, context-specific SRH knowledge.