Numerous scholars have argued that we are currently in a post 'tattoo renaissance' era wherein the practice has increasingly become a legitimate art form accepted by the American middle class. In order to facilitate this cultural transition, tattooed people legitimize their own tattoos through various narratives that ascribe deep semantic meaning to their images and words. Pulling from twenty-two in-depth interviews with tattoo removal clinicians, tattoo artists, people who regret at least one of their current tattoos, and people who have had their tattoos removed or altered, this paper contributes to the literature on the meaning and significance of tattoos in the lives of 21st century Americans. In particular, we aim to showcase that, in the current cultural context, wherein people feel a need to justify their tattoos with a level of profound symbolic meaning, tattoo regret abounds in a form distinct from that of previous generations. Drawing from a post-structuralist framework which understands tattoos as symbols, we discuss tattoo narratives as pervasive normative expectations and explore how people face potential dilemmas when they lack them, as well as when they subscribe static and absolute meanings to the words and images depicted in their body art. These narratives, and accordingly the tattoos themselves, become problematic as a result of the inability of tattoos to function beyond their capacity as symbolic representations. When people cannot reconcile or transcend the dynamic and relative nature of their tattoos' symbolic meanings, they feel regretful and sometimes opt for tattoo cover-ups or removals.