Jaylen and Emily’s story began in the halls of Clear Lake High School. Jaylen was starting his senior year and Emily her junior year when Jaylen decided to send Emily a Snapchat, simply saying, “Hey, what’s up?” They had never talked before, but that one message turned into weeks of Jaylen doing everything he could to get Emily to talk to him.
He sat right behind her in study hall, delivered her cookies, and even tried to learn about the crazy world of dance. What started as a simple Snapchat quickly became the beginning of something that just felt different.
It didn’t take long for them to realize just how much they had in common. They bonded over their love for Mexican food, sports, and how competitive they both could be. They admired how hard the other worked toward their goals, how deeply they cared about their families, and how naturally they both looked out for the people around them. What started as casual conversation quickly became something that felt easy, familiar, and meant to be.
Jaylen talked Emily into going on a “lake lap,” and they officially started dating on November 8, 2019. During COVID, they were lucky enough to spend most days together.
At the end of the summer, Jaylen left for college, beginning what would become five years of long distance. What followed were FaceTime dates that lasted late into the night, early-morning flights, and long drives just to spend a few precious hours together. Through it all, they wholeheartedly supported each other’s dreams of playing football and dancing in college, becoming one another’s greatest supporters no matter the miles between them.
Despite the miles, their love and commitment to each other grew stronger over the years. After Emily graduated in May 2025, she moved back to Iowa and into Jaylen’s apartment, finally closing the chapter on long distance. Just a few months later, they purchased their first home in Ankeny — beginning this new chapter side by side, excited for what was ahead and so grateful for how far they had already come together.
In May 2025, Jaylen and Emily traveled to Greece with Emily’s parents and brother to celebrate her graduation. The trip took them to Athens, Mykonos (ask Tyler how he liked it), and Santorini. On their first night in Santorini, Jaylen suggested a walk before dinner. He spent most of it glued to his phone, which left Emily a little confused.
What she didn’t know was that Jaylen was trying to coordinate with the photographer, who he couldn’t find. Eventually, he led Emily to a quiet overlook above the ocean, where, clearly nervous, he got down on one knee and asked her to marry him. Emily’s response was a repeated, “Are you serious?!” before, of course, saying yes.
Jared and Jamie had traveled all the way to Santorini for the big moment, spending most of the day tucked away at the hotel to avoid being spotted. When it was finally time, they joined Jay, Liz, and Tyler in a small shop across from the restaurant, all eagerly waiting to witness the proposal — only to miss it entirely, along with the photographer.
Emily was completely surprised when everyone gathered at the restaurant after the proposal — especially to see Jared and Jamie there. What she thought would be a quiet, romantic evening quickly turned into a joyful celebration. The rest of the trip was spent exploring Santorini and Paros together. The photographer never actually found them in time, so the proposal had to be recreated for photos — and somehow, that only added to the story. It was intimate, emotional, a little chaotic, and 100% unforgettable!