On March 7, 2017, REACH’s Youth Education Specialist participated in Wellesley High School’s Seminar Day. Seminar Day is an opportunity for community members, professionals, and students to lead workshops on a variety of real world topics. Students choose three different workshops to attend from a list of options. REACH’s workshop was called “Netflix and Chill? Intimacy, technology, and where to draw the line.” Overall 35 high school students and six faculty participated in activities that explored the role of boundaries and relationships in a world dominated by social media and technological interactions. The conversation began with an examination of what “Netflix and chill?” means and how diverse interpretations of a single term can impact relationships. Participants discussed the possibility and implications of misinterpreted intentions when using social media or texting to communicate. Students engaged in collaborative learning as they rotated around the room answering questions such as “What do we think of when we hear the word boundaries?” “Who do we establish boundaries with?” “How do we establish boundaries?” “How do we communicate in digital spaces that we are interested in someone?” “How do we communicate in digital spaces that we are not interested in someone?” We talked about and challenged gaps in generational and cultural understanding as we examined our interpretation of boundaries, some barriers to establishing boundaries, and the increasing dominance of screen to screen communication in the realm of interpersonal relationships.