Kaitlyn’s nomination letter captures the essence of his impact: the humor that softens disappointment, the encouragement that pushes students to go further, and the way he makes every student feel seen. Whether storming into a PSAT with accidental, catastrophically bad comedic timing or challenging a student to chase an idea “as far as it can go,” Dave creates a classroom where laughter and seriousness coexist—and where students discover strengths they didn’t know they had. Let’s get to know Mr. O’Brien a little bit more:
Dave grew up as the youngest of six children—four brothers and a sister—in a home where affection was often shown with a little teasing and a lot of humor. In a family that big, he admits that there wasn’t much room for ego; and through the teachings of his parents, they all developed a deep respect for humanist values that shape not just who Dave is, but how he teaches.
A graduate of Greece Athena High School, Dave headed to the University of Iowa where one of his brothers was a professor, in hopes of becoming a writer. While he enjoyed the experience, his academic discipline lagged behind his curiosity (aka: he didn’t always make it to class.) Eventually, he returned to Rochester and enrolled at St. John Fisher University, where he studied English, History, and Philosophy. It was there that his path began to clarify.
During a study abroad program at the University of Natal in South Africa, Dave spent eight months immersed in an academic environment that felt less like a classroom and more like an artist’s collective. Living and learning alongside peers, he took master’s-level courses in South African literature and participated in a shared model of teaching, with the students teaching one another, rotating through leading discussions and questioning texts. The experience ignited something. Teaching wasn’t just about content; it was about conversation, curiosity, and collective discovery. This experience gave him an appetite for teaching.
After graduating from Fisher, Dave pursued a Ph.D. at Loyola University Chicago. He ended up leaving the program ABD (all but dissertation) because somewhere along the path of research, publishing, and long-term academic inquiry, he realized that what mattered most to him was teaching, every day, with students in the room. When his wife began her medical residency at Strong Memorial Hospital, the couple returned to Rochester.
Back home, Dave became an adjunct professor at St. John Fisher, also working with the HEOP (Higher Education Opportunity Program), supporting students who were both economically and educationally disadvantaged. The work was meaningful. These were students hungry to learn, and Dave found deep satisfaction in helping them find confidence in their voices.
Harley entered the picture through another brother, Dan P ’11, ’17, ’27 (Middle School Math, 2004-present). Dave stepped in as a long-term substitute for English teacher Bob Kane (English and Hospice, 2003-2013). Bob’s classroom was warm and inviting. Dave enjoyed the students, admired Bob, and could see himself at Harley. When Bob decided to stop splitting his time between teaching English and hospice work, Dave applied for the newly opened English position. In the fall of 2011, he officially joined Harley.
The transition from college teaching to Upper School required a shift. Teaching at Harley demanded more day-to-day intentionality—more planning, more responsiveness, more attention to how students learn in the moment. But the heart of the work felt familiar. The content didn’t change as much as the form. Dave teaches from a guiding curriculum, but within it he finds freedom—to follow his interests, to adapt to the students in front of him, and to let curiosity lead.
One of his favorite concepts to explore with students is the idea of “metaphors we live by”—the understanding that metaphor isn’t just decorative language, but something wired into how we think and make sense of the world. Literature, for Dave, is always connected to life. As he often says, it’s about “connections to what we read and how we live.”
Quoting one of his favorite authors, George Saunders, Dave jokes that “Harley allows me to be weird.” His teaching style leans into that freedom. He’s less interested in delivering answers than in helping students learn how to ask better questions. Often, he’ll introduce a theme or idea and then step back, letting the class pursue the conversation wherever it leads—what he calls “direction by indirection.”
Some of the most inspiring moments come when he barely speaks at all—when students take over, engaging deeply with one another, offering complex ideas, listening closely, and building meaning together. He says these moments happen often at Harley.
Among the many texts he teaches, his favorite, As You Like It by William Shakespeare holds a special place. He returns to it again and again because it questions the idea of utopia—imagining a better world while revealing that every ideal deserves scrutiny. The Forest of Arden reminds Dave of his own family life: full of competing claims, irony, elasticity of language, and joy in conversation. The play’s loose structure, he says it is more talking than plot, resonates with him. It’s a reminder that meaning often emerges not from tidy conclusions, but from dialogue itself.
