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Mary Ann Messenger

“The mentoring program is an essential part of the mission, and it is the fundamental aspect of the school that makes us so unique,” Mary Ann Messenger, Upper School Director of Mentoring and theology teacher, says. “It is dedicated to helping the girl grow and develop as a whole person. While other schools have advisory programs, it’s very different from what we have – one-on-one mentoring where the mentor puts forth a tremendous amount of effort to get to know her mentee on all levels: to help her grow in virtue as a person, as a friend, as a student, as a daughter, as a sister. The results of mentoring here are so tangible, and you see that in the girls.”


At the heart of an Oakcrest education lies the one-on-one mentoring program designed to accompany girls as they develop into young women. Mary Ann Messenger, Upper School Director of Mentoring and theology teacher, says that this mentoring program is just one aspect of the school that she finds incredibly rewarding. 

“The mentoring program is an essential part of the mission, and it is the fundamental aspect of the school that makes us so unique,” she explains. “It is dedicated to helping the girl grow and develop as a whole person. While other schools have advisory programs, it’s very different from what we have – one-on-one mentoring where the mentor puts forth a tremendous amount of effort to get to know her mentee on all levels: to help her grow in virtue as a person, as a friend, as a student, as a daughter, as a sister. The results of mentoring here are so tangible, and you see that in the girls.”
As Upper School Director of Mentoring, Mrs. Messenger looks forward to spending this year continuing to enhance the program, and reemphasizing it throughout the school. 

“That’s what I’m most excited about,” she said, “to constantly and continually improve how we mentor the girls and continue to come up with techniques to help our faculty mentor effectively.” 

As the mentoring program continues to grow, Mrs. Messenger said an important goal is that mentors continue to partner with parents, “supporting them in the best ways possible in helping them raise their daughters.” 

Before coming to Oakcrest as a substitute teacher five years ago, Mrs. Messenger worked in the public sector for a decade after graduating with her Master of Science from Johns Hopkins University and a Bachelor’s degree from Mount St. Mary’s University where she studied business, economics, and finance. She then spent the next 22 years raising her children and homeschooling - and just when her youngest was in school all-day, she was told about a theology department opening at Oakcrest – a perfect combination of her passion for young people and her formation in the faith. 

“I love the Oakcrest community,” she said. “It’s so unique, so different from any work environment I’ve ever been in.” 

A favorite tradition of hers is how Oakcrest weaves the celebration of holidays – Halloween, Thanksgiving, Christmas, etc. – into the school culture in fun and exciting ways. 

In her interactions with the students, Mrs. Messenger said one thing she truly believes sets Oakcrest girls apart from others is the authentic friendships that they form with one another. 

“I see it in my classes,” she explained, “the girls want the good for the other, they want the good for their friend and they treat each other with great respect.”
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