Members of society today embrace multiple communication media for various purposes and intents. Text messaging has been identified as the medium of choice for continual relationship maintenance and text messaging from mobile devices overshadows all other media forms for the support of social connections. Text messaging is changing everything from how operators market their plans to how advertisers and service providers reach consumers. But just as technology usage of social media and internet access are different across generational boundaries, text messaging usage and habits may also be different for various generational groups. The majority of peer-reviewed research regarding text messaging usage habits has focused on adolescent and young adult users with less attention on text messaging usage habits by older adults; there is a scarcity of peer-reviewed research examining cross-generation text messaging habits and texting usage patterns. The primary goal of this study was to assess the similarities and differences in text messaging usage habits, purposes, and support of social connections differentiated by five of the commonly designated generational groups in America; the Post-War Silent Generation, Baby Boomers, Generation X, Millennials, and Generation Z. A mixed methods study provided data on the text messaging usage habits of members of the generational groups using a pool of adult college students, members of the researcher’s LinkedIn network, and data from a survey service to determine to what extent differences and similarities exist between users’ text messaging usage habits within each generational group. Results indicated generational group membership has a significant effect on a participant’s messaging volume (UV), text messaging partner choices (TMPC), and text messaging social habits (SH), regardless of gender, education level, or employment status. The older the generational group, the more likely they are to prefer talking over texting and to have issues with the device interface. The Post-War Silent generation texts their spouses the least of any group, while Generation X texts their spouses the most, and all generational groups with the exception of Generation Z would limit texting while driving. Generational characteristics seem to have some influence over texting behaviors. Contributions to the existing body of knowledge in the human computer interaction field include an investigation of factors that contribute to each generational group’s willingness to embrace or reject the text messaging medium, and an investigation into the into how each generation views and exploits the texting medium.