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, where Caitlin, ever the gracious competitor, let Ryan win in a game of darts. 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. It was a whirlwind introduction to her close friends, but Ryan handled it like a pro, charming everyone with his easygoing nature and 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. 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 going on vacation in the summer of 2024, but she finally accepted that they should save money for a house instead. Then, one evening, he surprised her by announcing they’d be going to Grand Cayman in July. Hopeful that this would be their engagement trip, Caitlin couldn’t shake the feeling that it was too obvious. But then he took her to look at engagement rings and bought the Proposal Prep box, so her suspicions started to grow.

In preparation of the trip, Caitlin had meticulously planned an itinerary for each day, filled with lots of fun activities. Just before they left, Ryan casually mentioned that he had planned out the entire day for July 10th. Caitlin, being coy, pretended to be a little upset that he waited until the last minute to let her know, trying to maintain the illusion that she wasn’t onto him.

The day of the proposal arrived, and Ryan was rushing Caitlin to get ready (what’s new), all the while hiding the excitement bubbling beneath the surface. Unbeknownst to her, he had booked a cabana for the day, complete with champagne and all! He also hinted that she would want to look good for dinner, which only added to her suspicion.

As soon as they arrived at the restaurant, Caitlin noticed a photographer waiting at the hostess stand, which made her heart race with anticipation. The host began walking them to their table, which was beautifully set on a bluff overlooking the ocean, with rose petals leading the way. It was a scene straight out of a fairy tale!

As soon as they reached the table, Ryan couldn’t wait and got straight down on one knee. Despite having suspected that a proposal was coming, Caitlin was overwhelmed with emotion and cried like a baby, somehow managing to say ‘Yes’ through her tears. It was truly the most magical moment that marked the beginning of their next great adventure together.