Independent school environments offer relatively small faculty-to-student ratios that afford significant time and opportunity for quality interactions with students. Beyond the standard expectations of shepherding students through a course of study, encouraging them to participate in extracurricular activities aligned with their interests, and teaching them about respectful community living, independent school educators often serve as sounding boards and confidants regarding the students' personal lives. Engaging young people in conversations about their intimate and sexual relationships, however, can be a particularly challenging role for faculty and advisors, many of whom are hesitant or lack confidence in talking with students about these issues. Moreover, teenagers today socialize in a world in which cell phones and social networking sites are common tools for meeting and finding out about each other, forming and conducting relationships, "hooking up" (with all the varied definitions that phrase can imply), and even breaking up. The widespread use of these "new" technologies to conduct the business of relationships is territory that feels very unfamiliar to many faculty and advisors. In this article, the authors describe how adults can translate their "old fashioned" wisdom about relationships to fit online social networking and other technologically based ways of communicating and relating. They offer four broad questions that can assist teachers and advisors in guiding conversations with students about their relationships. Within each section, they offer a sampling of specific discussion starters and take into account a range of technological means of communication commonly used by students today.