Teaching Math 1E and 2E to sixth and seventh graders, Math Teacher Ms. Jessica Gentry knew she had to wear a standout costume for Halloween. Her solution: a box of tissues and a jersey sporting the number seven. A “sick-seven,” she explained.
Since the spring, Ms. Gentry has served as the long-term replacement for Math Teacher Ms. Christina Wong. She will step down after winter break when Ms. Wong returns from maternity leave.
In the meantime, Ms. Gentry has fit right into the Bishop’s community, bringing energy to the classroom and a willingness to understand her students, even their childish humor. Every day during office hours, students fill Ms. Gentry’s classroom. Ella Xie (‘32) said she often stops by “because her office hours are awesome, and a lot of my friends are here, and it’s always very chill.”

Ms. Gentry’s teaching career began with her love for dancing. A former professional dancer, Ms. Gentry said, “My dream was to book a tour, but I also needed money. So I thought to myself that teaching would be perfect.” School days end early, she explained, so she could take all her dance classes, and she would have the summer off. “The perfect lifestyle,” she joked.
Ms. Gentry discovered that she enjoyed teaching because seeing her students grow was so rewarding. “But classroom management and school politics were frustrating,” she explained. She pivoted again and became an educational therapist, a professional who helps students with learning differences, so she could continue working with kids on her own terms.
Ms. Gentry elaborated on the difference between being a teacher or tutor and an educational therapist. Teachers and tutors have a curriculum to follow, she explained, but “I see how a student’s brain works and where their strengths and weaknesses are.” She reminds her students that “you just have to learn how you learn.” Her positive affirmation improves both the in-class performance of her patients and their mental health.
Despite the meaningful impact of her work, Ms. Gentry missed the school community. She decided to apply for a long-term leave replacement because it was not a full commitment, and she had yet to teach at Bishop’s.
Ms. Gentry explained that she was impressed by the middle school math department and thought, “I’d be really lucky to learn from these people. And I could learn so much and just become a better person.” She compared the job to a paid internship because she would not only teach her students but also learn from them and the faculty.
“I also knew, even if it was really not the best experience, it had an end date,” Ms. Gentry explained. However, she fell in love with Bishop’s, a bittersweet result, and she added, “Of course, when it’s just a temporary thing, you’d want to stay.”
The Bishop’s Math Department was impressed by Ms. Gentry. Chair of the Math Department, Ms. Catherine Beamer, highlighted Ms. Gentry’s “kind, enthusiastic, and warm personality” and her ability to “immediately make other people feel at ease, whether they’re a student or a colleague.” Ms. Beamer added that Ms. Gentry has “seamlessly integrated herself into the community” and is “a big team player and wants to help out and contribute in whatever way she can.”
“We’ve been really grateful to have her, and we’re sad to see her leave. We would love to find a way to keep her here.” Ms. Beamer concluded.
Acting as a replacement has also allowed Ms. Gentry to take initiative in her teaching. Unlike a substitute who might put work off until the actual teacher returns, she makes her own informed decisions, even when she is not entirely sure what the usual teacher would do. She compared her temporary role to being the “cool aunt,” someone who can still be an effective teacher while giving her students more freedom.
Ms. Gentry’s students love her approach to teaching. Gabrielle Mutusiak (‘32) said that “Ms. Gentry has made me see math in a different way” and has made her “embrace math more because she makes class fun.” Sehra Suri (‘32) elaborated, explaining that in her 1E math class, students made customized math bingo games to learn products.
Sehra also said that after students have completed their classwork, they can choose whether to do homework or an alternative assignment, like math puzzles and games. She remarked that “options make classes more interesting.”
Ms. Gentry’s students are also the reason she loves teaching. Her favorite part is when her students tell funny stories, she explained. When working with recursive and explicit sequences, she asked her class, “What do you think explicit means?” and one student responded, “When my dad plays games with his friends, there’s a lot of explicit language.” “It’s just fun to see their personalities [through anecdotes],” she said.
Ms. Gentry’s students appreciate her kindness. Sara Park (‘32) described her personality as “optimistic and friendly,” and Alex Rodriguez Bader (‘32) agreed, saying, “she’s always there to help, and she’s very supportive.” Gabrielle added that “Ms. Gentry encourages office hours” because “It’s not a crime to not know the answer.” Blake Hay (‘32) concluded, “We all want her to stay.”
Ms. Gentry connected her aim back to an anecdote from her high school days when she struggled to understand the concept of a derivative. She explained, “My teacher couldn’t understand what I couldn’t understand. So I thought, ‘I’m going to die in this class.’” As a teacher, she now draws on those experiences to better support her students. “I think a better teacher is someone who knows how to teach rather than someone who just understands something innately,” she explained.
Outside of Bishop’s, Ms. Gentry also participates in a variety of activities. She coaches Lagree fitness classes and also does orienteering once a month, a race to find a series of points using a compass and a map. “I know running is good,” she explained, “but I can’t [run] unless there’s a goal,” which drew her to orienteering.
Flexibility classes at circus school also fill Ms. Gentry’s free time. “I used to be a dancer, so I like to try to be around creative people,” she said, “people who don’t care about norms and are who they are.”
Whether she’s planning math games for her students or navigating her next orienteering course, Ms. Gentry’s adventurous spirit inspires her students. Her genuine nature will be missed dearly by her students and colleagues alike. After all, it takes a special kind of dedication to keep up with the humor of sixth and seventh graders.
