The primary aim of this study was to examine how and why adolescents make decisions regarding whether to conduct their communication via texting versus calling features of cellular telephones. Individual semistructured qualitative interviews were conducted with 41 adolescents aged 14 to 18 focusing on their use of calling and texting when communicating with friends, parents, and romantic partners. Through grounded theory analysis, a conceptual decision-tree emerged depicting a process of decision making based on communication content, communication partner, and situational limitations. Further analysis indicated that the adolescents consistently perceived texting as easier than calling in ways that were meaningful to their everyday lives. Findings reflect the complex interweaving of logic, personal preference, and concession to social constraints that goes into adolescents’ choices to call versus text.