This chapter explores how teens use new media like mobile phones, instant messaging, and social media to form, maintain, and end intimate relationships. It discusses how teens craft complex emotional realities online and offline. New media allows teens to casually flirt and communicate beyond their parents' oversight. When in relationships, teens use technology to demonstrate affection publicly and privately and have expectations of frequent contact. Breakups are often mediated online through status changes or public posts, and teens monitor each other after breaking up. New media both increases vulnerability through monitoring but also allows teens control over emotional exposure.