Selected from three senior and five junior finalists, this year’s Guerin Prize winners Natalie ’16 and Car ’16 will have the opportunity to meet their heroes for their respective essays on renowned actress and writer Tina Fey and United States Navy four-star admiral Michelle Howard. Natalie and Car each wrote about their role model because the two women are not only inspirational figures but because they have made strides in male dominated fields.

Natalie was introduced to Fey when she watched Fey’s comedy Baby Mama in fifth grade and has followed her career ever since.

“I actually opened my essay talking about that [movie]. After seeing that movie, for some reason, I was really interested and intrigued by female comedians and saw myself as being like them,” Natalie shared.

So, according to Natalie, choosing Fey was a no-brainer.

Natalie, who helped direct Drama Ensemble’s play It’s a Girl! this year, wants to pursue a multi-faceted career in the entertainment industry, like Fey — writing, directing and acting. In her essay, Natalie emphasized Fey’s ability to excel in a wide range of pursuits, from writing a New York Times’ best-selling book, Bossy Pants, to acting in her own TV sitcom 30 Rock. Natalie also said she is in awe of Fey’s capability  of accomplishing this in a heavily male environment.

“She’s been ridiculously successful in a male-dominated field — the entertainment industry, especially comedy, is very male-dominated. All of the gains she has made for women have been done through comedy. Because of her, SNL for a long time became a very female-heavy comedy show. She was a head writer, and she helped to make that change,” Natalie enthused.

Natalie also admires Fey’s friendship with fellow female comedian Amy Poehler, deeming them the “comedy queens.” Their closeness highlights an important female bond — women building each other up rather than tearing each other down.

Upon meeting Fey, Natalie hopes to talk to Fey not only about her experiences as a woman in comedy but also about the prospects of women in such a male-dominated field. She also noted that she would probably start crying out of happiness.

“I really want to ask how she sees the future of women in comedy… [I would like to] talk to her about all of her life experiences. I just want to be her best friend. I know everyone does,” Natalie said.

Like Natalie, Car said she knew exactly who to write about when the essay contest was announced last November. Howard was both the first female four star admiral in the Navy and first African-American female four star in the military and currently is the 38th Vice Chief of Naval Operations, the second -highest -ranking position in the Navy. Car admires Howard’s trailblazing mentality and service as a woman in a male-dominated career.

In fact, Car finds inspiration from Howard’s experiences. Howard attended the Naval Academy, and Car, the sole diver on the Marlborough Varsity Swimming and Diving team, plans to apply to the Naval Academy later this year. Car compares the number of women in the Naval Academy during Howard’s time and today. Although it is double the amount of women in the 1980s and 1990s, today only 20% of the Naval Academy’s graduating class comprises women.

Car aspires to join the explosive ordnance disposal (E.O.D.) operations, a special operations team that diffuses bombs on land and underwater. According to Car, there are only about 10 women out of thousands of people working in E.O.D. operations. Although Howard works in service warfare operation, not E.O.D., Car said she would appreciate Howard’s guidance about maintaining a sense of self in such a conforming and male environment.

“I mostly just want her advice because I’m applying to the Naval Academy… [The Navy is] still a very dominantly male environment. Coming from Marlborough, that’s something very foreign to [me]. So, I would ask her questions about how to deal with being in an all-male environment and keep your sense of ‘this is who I am,’” Car commented.

Director of Admissions and administrator of both the Guerin Prize and Visiting Scholar programs Jeanette Woo Chitjian said she believes this mentorship quality between prize winners and role models makes the prize so special.

“There’s the opportunity to ask these women: ‘How did you get on this path? And what advice can you give me? Because I’m also on this path’,” Woo Chitjian expressed.

With the help of former two-time trustee and donor of the prize Rick Guerin, Woo Chitjian is currently early in the process of connecting the winners with their role models.