Dating violence is a significant social issue among U.S. teens. As digital media (social media and mobile phone) use increases, scholars and practitioners become more concerned about these media being used for abuse in dating relationships. A pattern of abusive digital media behaviors meant to pressure, coerce, threaten or harass a dating partner, termed "digital dating abuse" (DDA), is a common form of dating violence and the subject of an emerging literature on how teens use digital media in their relationships. The current study sought to understand how teens conceptualize their worst experiences of DDA and how they respond to these experiences. A sample of 262 high school students completed an online survey including open-ended questions about their "worst digital dating abuse" experiences. Content analyses of these open-ended responses found that Public Insults, General Insults, Violations of Privacy, Rumors, Break-Ups, and Pressure for Sex/Sexual Photos were the most common form of Worst DDA reported. Girls were more likely than boys to cry or be upset in response to these experiences. Teens were more likely to tell their peers than trusted adults about their Worst DDA experiences. These results can inform prevention and intervention of youth experiences of DDA.