Challenging the taken-for-granted status of canonical authors, especially Shakespeare, is difficult, but not impossible. This research offers a glimpse into the inferential processes of a group of grade ten students from diverse backgrounds who read unfamiliar passages from Shakespeare. The findings reveal a complex picture of meaning-making, involving a variety of factors that play role in the students' reading comprehension. The most crucial insight is the finding that subjective interpretations seem to hinder independent understanding and appreciation of Shakespeare's texts beyond the literal level. Our research, conducted in a large, urban, culturally-diverse high school in Western Canada, shows that students tend to rely on uncritically absorbed bits and pieces of background information or popular culture references, as well as overgeneralized understanding of previously read Shakespearean texts, to form opinions about the author, which often carve an interpretive lens, colouring the reconstruction of the characters' experiences in subsequent encounters with his works. The study juxtaposes actual experiences of students reading Shakespeare to culturally endorsed attitudes informing curriculum decisions and policies, as well as prevalent teaching practices in the high school classroom. Finally, it asks if teachers need to look at personal connections not as a strategy that leads to an analytic engagement, but as a form of analytic engagement, affirming that critical reflection is a competence that requires careful nurturing and guidance.