Over his eight years at the school, upper school English teacher Kyle Dennan’s classroom walls have been covered in years of memories, including pictures of inside jokes and height charts. As he prepares to depart at the end of the academic year, those physical markers reflect the deep relationships he has cultivated both as an educator and a mentor. 

Looking back on his near-decade of on-campus teaching, Dennan notes that the most impactful moments often happen when a student truly connects with the material. 

“My favorite thing is when a student rises to the challenge and goes forward to continue reading things on their own. That’s really rewarding,” Dennan said.

While academic breakthroughs stand out, he considers much of his impact to have occurred outside the traditional English curriculum. For the past eight years, Dennan has served as a faculty advisor, guiding two groups of eight students through their high school journeys. Watching that personal transformation from freshman to senior year has been a cornerstone of his teaching career.

 “I love just watching my advisees grow as people,” Dennan said.

That growth is something his advisees credit directly to the unique environment Dennan creates during homeroom. Sophomore Amelia Paine, who is his advisee, notes that he has built a space rooted in connection. From the check-in ritual of “rose, bud, thorn” to competitive rounds of the card game Taco Cat Goat Cheese Pizza, Dennan transformed the standard advisory period into a tight-knit family. 

“There’s a great sense of community, and just fun in general,” Paine said.

Beyond the games and traditions, Paine emphasizes that Dennan’s consistent, daily support provided a reliable anchor throughout the stresses of high school. Whether students needed academic advice or simply a sounding board after a difficult day, his door remained open for any conversation. 

“He’s always very kind, he’s thoughtful, and he lets me talk to him about anything,” Paine said.

Next year, however, that familiar classroom environment will change as Dennan relocates to Montclair, New Jersey, where he will join the faculty at Montclair Kimberley Academy. The move brings him closer to his sister and marks a major personal transition after nearly a decade in his current role. Despite the excitement of a new chapter, Dennan admits that leaving his students will be a difficult adjustment. 

“I’ll miss the students. At St. John’s, they are tremendously engaged and intellectually curious,” Dennan said.

The move represents not just a change in geography, but the conclusion of a foundational era in his teaching career. Having spent nearly a decade collaborating with the same faculty members and watching multiple groups of students graduate, the farewell is bittersweet.

“I’m super happy here, but it’s just time to move on,” Dennan said. 

Dennan’s best memory throughout his career occurred during his first year at the School.

“One of my groups of sophomores collected a list of quotes and just put things that had happened over the course of the year,” Dennan said. “When I came in on the last day, they had written them on the board. It was a great surprise, and they had a cake.”

Even though he has been happy throughout his teaching tenure, Dennan is most excited about the new career he is embarking on. As he concludes his time in Houston, Dennan leaves one message with the student body. 

“Keep reading, re-read, and just read all the time.”