From High School Sweethearts to Forever: The Engagement Session of Brianna and Kyle in Cleveland, Ohio

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Kaitlyn Smale's picture
Written By
Kaitlyn Smale
Date
April 13, 2026
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Some love stories begin with a grand gesture—but for Brianna and Kyle, it all started in the most familiar place: high school. “Kyle and I met in high school!” Brianna shares. “We did marching band together and saw each other frequently due to practices and performing at the football games.” What began as a simple crush quickly turned into something more. “I had a crush on him and asked to hang out after school,” she says. “After spending time together we realized that we loved being together—and the rest is history.”


When it came time to propose, Kyle created a moment that felt straight out of a fairytale—at Walt Disney World Resort. “Kyle proposed to me on Mickey & Minnie’s Runaway Railway,” Brianna says. “My family was sitting in the row in front of us, and he popped the question during the final firework scene on the ride.” For Brianna, the setting couldn’t have been more meaningful. “The theme parks hold a special place in my heart since I grew up being a Disney girl,” she shares. “That ride in particular always reminded us of ourselves, with Mickey and Minnie symbolizing our own relationship.”

 

When it came to the ring, Brianna had a clear vision—and Kyle made sure to bring it to life. “I knew exactly what I was looking for in my engagement ring,” she says. “I spent time showing him pictures and describing what I liked, and once I left the room he wrote everything down so he wouldn’t forget.” Though he played it cool, Kyle was paying attention to every detail. “In reality, his aloofness was all a ruse,” Brianna laughs, “all the while ensuring that I would receive the perfect ring!” The result is a truly one-of-a-kind emerald gemstone on a gold band. “I love the stones and the overall look—it feels very classy and unique.”


For their engagement session, Brianna and Kyle wanted a setting that felt different from their future wedding day—and meaningful to their story. “We both grew up in the Cleveland area,” Brianna says. “We wanted to make sure we captured a city atmosphere since we’re having our wedding at a barn surrounded by nature.” They chose Cleveland as the backdrop, embracing its architecture, history and cinematic feel. “Kyle has always been fascinated with architecture and history,” she shares, “so downtown Cleveland provided the perfect backdrop for our vision.”


Inspired by classic urban romance films, the couple leaned into a timeless, movie-like aesthetic for their session. “We wanted to take some inspiration from urban rom-com movies,” Brianna explains. With their session taking place in early January, their wardrobe choices reflected both the season and their vision. “We decided on trench coats, dress pants and turtleneck sweaters,” she says. “We also love dressing in similar colors and looks, so we wore matching styles.” The result was a cohesive, romantic gallery that feels both elevated and effortlessly personal!


While their engagement session embraced the energy of the city, their wedding day will reflect something softer and more serene. “When we got engaged, we both knew we wanted a cozy and naturalistic setting,” Brianna shares. Inspired by a love of intimate, peaceful spaces—and a touch of cinematic influence—their vision is beautifully unique. “Being a huge Twilight fan, I strive to emulate a rustic and ‘cottagecore-esque’ ceremony like the movie had,” she says.


As they plan their wedding, Brianna and Kyle are embracing both the excitement and the challenges that come with it. “So far our wedding planning experience is going very well!” Brianna shares. “It’s definitely a lot to plan and we both get stressed at times, but overall we’re enjoying this short and special time of being engaged.”

 


 

 

 

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