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Kaitlin & Jack

10.3.2026 • Cleveland, OH
20 Days To Go!

Kaitlin & Jack

10.3.2026 • Cleveland, OH
20 Days To Go!

Our Story

Our story began long before either of us realized it would become a love story. We attended the same high school, shared mutual friends, had siblings who went to school together and spent years orbiting the same circle without ever knowing exactly where it would lead.


Then came 2020.


After The Unicorn closed, Katie began spending more time at Jailhouse with mutual friends Janet and Jason, Jill, Greg and Jeremy. One night, Jack walked into the bar, and Katie saw him for the first time in years. Her reaction was immediate enough that she texted Jill and asked, “So, what’s up with Jack? Is he single?”


There was just one problem: Jack traveled frequently for work, played in a band and seemed entirely too cool to ever settle down and become a relationship guy.


As it turns out, Katie could not have been more wrong.

Our first official date was a group trip to the House of Blues. A few weeks later, a karaoke night sealed the deal, and by the end of April 2022, we were officially dating. Karaoke has remained a supporting character in our relationship ever since—and, for the record, we always kill it.


By October 2022, we knew this was becoming something serious. We took our first road trip together, driving all the way to Key West and back. Anyone who can spend that many hours in a car together and still want another road trip has probably found their person. In April 2023, at the Piston Power Show, Jack asked Katie to move in with him.


Since then, we have built quite the travel résumé. We have driven to Key West twice, taken a spooky road trip through Salem and into Maine and Vermont, traveled to Ireland, driven to Colorado for a ski trip and squeezed in countless smaller adventures along the way. Wherever we go, we inevitably find a karaoke bar—and somehow, even the drives with no destination become some of our favorite memories.


On July 11, 2025, Jack pulled off the ultimate surprise.

During one of our Patio Par-Tee events at Brentwood, Jack called Katie onto the stage. With her birthday coming up on July 16, everyone assumed he was about to lead the crowd in singing “Happy Birthday.” Instead, Jack pulled out a cloth napkin, carefully placed it on the ground, got down on one knee and asked Katie to become his wife.

It could not have been more perfect. These live-music nights were something we had started building together the previous summer, and just a few weeks earlier, Katie had told her dad how incredible it would be if Jack proposed there someday. Jack wisely waited until the morning of the proposal to ask Kevin for his blessing—giving him as little time as possible to accidentally spill the beans.


The surprise worked. Katie never saw it coming.


Today, we share a beautiful life with our dog, Dodger, and our cat, Penny. We complement one another in our careers, challenge each other to keep growing and always push one another toward the best versions of ourselves. Katie admires Jack’s patience, loyalty, steady hand and willingness to teach anyone who wants to learn. Most of all, she loves the way he strives to leave every person and every place better than he found them.


We are partners, adventure buddies, karaoke champions and truly the best of friends.


On October 3, 2026, we begin our favorite adventure yet.