It all started with a (couple) right swipes, and a lot of GIFs, in January of 2020. Ryan and Caitlin’s first date was on February 1st. Caitlin let Ryan win in a game of darts at what is now a Levi’s store. Little did they know, this moment would be the start of a great love story.

Just a week later, Ryan got initiated into the girl gang when he attended Caitlin’s 30th birthday celebration (#RIP30s). It was a whirlwind introduction to her close friends, but Ryan handled it like a pro, charming everyone with his easygoing nature and, most importantly, buying lots of drinks!

Ryan and Caitlin continued to date on and off for the next year and a half, navigating the ups and downs of life and love during COVID. Slowly but surely, Ryan came around and realized that Caitlin was the best, and the rest, as they say, is history.

They moved in together in downtown Greensboro, where their lives truly began to intertwine. Ryan embraced his new role as a dog dad to Caitlin’s beloved dogter, Abita, while Caitlin had the joy of meeting Ryan’s son, Austin. Together, they created a little blended family, filled with love, laughter, and plenty of adventures.

They’ve cruised the Caribbean, sipped wine in Sonoma, swam cenotes in Mexico and attended countless weddings together. From the beach to the mountains, the pumpkin patch to the Christmas tree farm, and everywhere in between, they built countless memories as their bond deepened. Sure enough, they fell madly and deeply in love.

Caitlin had been nudging Ryan about taking a summer vacation in 2024 but eventually accepted that saving for house was the smarter choice. Then, one evening, Ryan surprised her by announcing a July trip to Grand Cayman! Hopeful that this might be the trip, Caitlin couldnt help but think it all felt a little too obvious—until Ryan started dropping some serious clues. First, he ordered the Proposal Prep box. Then, he took her to look at engagement rings. Caitlins trademark indecisiveness led to Ryan not being able to order the ring that day, so she assumed there was no way it would arrive in time for their vacation. Her hopes started to fade, and she began doubting whether a proposal was really in the cards.


Caitlin had meticulously planned out an itinerary for each day of the trip. But just before they left, Ryan casually mentioned that he had planned out the entire day for July 10th. Caitlin, being coy, pretended to be annoyed about the last-minute reveal—though deep down her suspicions returned that this might actually be their engagement trip.


On the big day, Ryan woke Caitlin up and urged her to get ready quickly (nothing new there), while secretly brimming with excitement. Unbeknownst to her, he had booked a private cabana for the day, complete with champagne, and causally hinted she might want to dress up for dinner. At this point, Caitlin was all but certain something special was coming.


When they arrived at the restaurant that evening, Caitlin immediately spotted a photographer waiting at the hostess stand, and her heart began to race. As they started walking to their table, she noticed that it was set on a bluff overlooking the ocean, waves crashing against the rocks, with a path of rose petals leading the way—it felt like a real-life fairy tale!


As soon as they reached the table, Ryan couldn’t wait a second longer. He dropped to one knee, and Caitlin overwhelmed with emotion, burst into tears—so many, in fact, the photographer later said she’d never seen a bride cry that much before! Through all the happy tears, Caitlin somehow managed to squeak out a YES!


It was a magical, unforgettable night and the perfect beginning to their next grand adventure together.