Digital technology has become central to how adolescents explore their developing sexuality and form relationships with peers, including romantic and sexual relationships. Interviews with 110 high school and college students in the Northeastern USA identified how digitally mediated communication is a fundamental part of adolescent flirtation practices, with young people making use of digital affordances to mitigate the interpersonal risks associated with flirtation. The 'screen' is seen as a protective barrier against the emotional vulnerability and embarrassment that can occur during in-person flirtation. Gender and sexual minority youth also appreciate how digitally mediated intimacy protects them from threats to physical safety in a hetero-patriarchal world. By contrast, adults perceive cell phones and social media as sites of risk for young people. Teenagers are portrayed in the media as the hapless victims of technology rather than agentic creators of digital sexual cultures. Their digital interactions, especially when sexual in nature, are highly regulated and subject to social control. This focus on technological risk blinds educators to exploring the ways in which new technology is integrated into adolescents' socio-sexual lives. To be effective, school-based sex education must engage creatively with the role of digitally mediated communication in adolescents' romantic and sexual lives.