The fates collided when Caitlyn sent Tom a “rose” on Hinge (obviously because of his piña colada–making skills). Almost instantly, they matched and within a day were already planning their first date. That date, just a few days after Tom’s birthday, was a gorgeous, sunny August afternoon. They met for drinks at the Boathouse at Sunday Park. Tom remembers Caitlyn “floating” down the stairs like an angel, while Caitlyn remembers how effortlessly cool Tom looked, casually leaning on the rail with his backwards hat, waiting for her. Their first date seemed to go on forever… they were both hooked from the start. The rest of their story unfolded just like that first day: fast, fun, and full of love. In their first few months together, they saw Morgan Wallen live in Charlotte, went to Virginia Beach to see Tom’s brother perform in Mean Girls, flew on a private plane to Blacksburg (thanks, Megan & Michael!), and countless other adventures.

Much like the end of 2024, 2025 was fast, fun, and full of adventure. The year kicked off with a romantic Valentine’s getaway to the Cavalier, where Caitlyn’s love of adrenaline met Tom’s fear of heights in the ultimate compromise, indoor skydiving! Between a whirlwind of travels, they also prepped Tom’s house to rent and officially moved in together. By summer, they were celebrating their one-year anniversary with their first big trip, an unforgettable eight-day cruise through the Bahamas, Dominican Republic, Aruba, and Curaçao. Then came October 26, 2025. A day Caitlyn thought would be a simple fall outing to Carter Mountain after a busy work season. Little did she know, Tom had been planning everything behind the scenes (while letting her think it was her idea, of course). Insisting they arrive early to “beat the crowds” and take photos before it got busy, Tom suddenly dropped to one knee. After a very enthusiastic “yes,” Caitlyn looked up to see both of their parents cheering from the hilltop. It was the most perfect proposal, filled with love, family, and breathtaking views. Now, they’re happily planning their dream coastal wedding with immediate family in May. Between all the excitement, they’re soaking up the little moments… laughing endlessly, talking each other off ledges, and being each other’s biggest fans every step of the way.