This paper presents findings from an in-depth qualitative investigation of adolescent females and males residing in two low income urban settings in India – a slum and a resettlement colony in Delhi. This paper sheds light on the widening rift in the perceptions of parents and experiences of adolescents in the area of sexual behaviour. Results suggest that gender double standards and power imbalance powerfully influence socialisation patterns, expectations and behaviours of young females and males. Despite stringent controls on the mobility and activity of unmarried youth and particularly females, opportunities do exist for sexual relationships, sometimes with adverse consequences for young people’s health and lives. Liaisons tend to be secretive and awareness of safe sex and the protective nature of condoms are limited. Parental perceptions of and confidence in their ability to control and protect their adolescent daughters from dangerous relationships are clearly unfounded as opportunities unfold for increasing interaction among young people. Indeed, interaction and intimacies between boys and girls occur quite frequently and adolescents report a host of opportunities available to them to build friendships and sexual relationships. Findings argue for programmes that apprise parents and other adult gate-keepers of adolescent behaviours and sexual health needs while at the same time equipping adolescents to make informed, safe and wanted choices in their sexual lives.