Tyler Darden wins TEAM Westport Essay Contest, encourages sensitive conversation


Darden reads his essay aloud for an audience at the Westport Public Library. His piece centers around his experience coming to terms with his sexuality.

The 2023 TEAM Westport Teen Diversity Essay Contest challenged high school students to focus on one thing: dialogue. 

Tyler Darden ’25 took the prompt and ran with it, elegantly reflecting on his interactions with people of “different racial, ethnic, religious and/or LGBTQIA+ identities and/or perspectives,” according to the Westport Library website. He and two other Westport teens were honored as winners of the competition at the Westport Public Library on April 18. Darden placed first, winning $1000 in prize money. 

According to Darden, his essay was based on the concept of “coming to terms with [his] sexuality against the backdrop of traditional gender norms.” 

He saw the essay contest as a vehicle for self discovery and awareness. 

“I thought it would be a great opportunity to explore my own journey towards self-acceptance, and be vulnerable in a way I hadn’t been before,” Darden said. 

Immediately, Darden felt drawn towards the prompt. 

I thought it would be a great opportunity to explore my own journey towards self-acceptance, and be vulnerable in a way I hadn’t been before,

— Tyler Darden ’23


As soon as I read the prompt, I knew I wanted to write about my own experiences,” he said. “Specifically, reflecting on an event from childhood which shaped how I came to terms with my sexuality.”

The writing process felt incredibly freeing for Darden. 

“When I started writing, I couldn’t stop. With every word I put on the page, it felt like I was sewing closed a wound.”

The task also required writers to look beyond their personal experiences and brainstorm implementable strategies for the Westport community to better support dialogue surrounding diversity and identity. The task asked writers, “What specific actions would you suggest that individuals, schools, and/or town entities in Westport take to promote good-faith dialogue, reduce bias, and foster understanding?”

Darden appreciated this angle of the prompt. 

“[I] wanted to suggest how our schools can help to foster understanding and acceptance so others don’t endure the same struggles,” he said. 

Darden beams with TEAM Westport chair Harold Bailey, Staples High School principal Stafford Thomas and Westport’s 1st Selectwoman Jen Tooker.

At the awards ceremony, Darden and the two other honorees read out their articles to an enraptured audience. Only that night did they find out who had won the first, second and third place prize, so nerves were running high. 

It was full of anticipation […],” Darden said. “When they called my name, I was terrified […] but once I started reading my essay I felt full of pride.”