While Raegan and Ryan knew each other since middle school, they first got to know each other during junior year of high school. That year, their friendship began and continued until senior year. Approaching the end of senior year, Ryan was informed he would be taking Raegan to prom by one of Raegan’s friends. While this was news to Ryan, he was happy to hear it as he had liked her for some time. He then asked her to prom spelling it out in cupcakes, knowing she enjoyed baking for their friend group. After prom, they remained friends until the final hangout before leaving for college. There, Ryan decided to tell Raegan, before he went to Alabama and she went to Delaware for school, that he had liked her to find out if she had felt the same. Her response, while predictably not verbose, told him all he needed to know. From there, it seemed, they would be the “one that got away” as they were about to be 941 miles and 14 hours apart. They kept in touch over the years and were always secretly excited to see each other. Unfortunately, they lost contact through the final year of college until finally seeing each other again after college ended. To both of their delight, they discovered they were both going back to school in the south. This time only 3 hours and 194 miles apart. On Raegan's ride home, she got a text from Ryan. It did not take long for him to officially ask her to be his girlfriend, and three and a half years later, he asked her again, this time, to be his wife.

Ryan knew for a while that he would ask Raegan to marry him in Italy. He had been planning a trip to honor his late Mamon (grandmother) and Baba (grandfather) as they loved to travel. They had been married for 50 years which made the idea of proposing on a trip in their honor that much more special. As the trip approached Ryan knew Raegan was likely suspecting a proposal, so he decided to try and throw her off his trial. Asking simple questions like “you have two years to propose after asking someone’s parents right?” and “should we go look at rings in that shop?” during the trip helped make it less obvious. Ryans plan seemed flawless. He had hired a photographer, set the spot (Gardens of Augustus in Capri), and the date (October 21st). Everything was going to plan until the night before they were to arrive in Sorrento, his photographer said he could not go to Capri the following day due to bad weather. Ryan did not sleep much that night. Using bathroom trips, annoying work colleagues, and dinner reservations (one of which they ended up using after the proposal) as excuses Ryan was able to message places in Sorrento without seeming too suspicious to Raegan. To his dismay, places were either closed or did not speak enough English to properly communicate. Raegan began to get upset with Ryan’s pretend work disturbances and wanted him to stop using his phone. As a final act of desperation, Ryan asked his photographer if he knew a spot near their hotel they could use as he could no longer use his phone. To his delight, the photographer found a beautiful location near their hotel in Sorrento. Just as everything seemed to work out, their bus was delayed. Now Ryan knew there was no way to convince Raegan to put on a dress and run down to an unspecified location without seeming suspicious. He decided to tell her about the photographer, however, he told her he had booked a private photo shoot and that the bus delay was going to make them miss it unless they ran. So they ran. On the way, Ryan texted the photographer she knew about the photoshoot but not about the proposal. Once the photographer said “now hold hands and I’ll get some candid photos” Ryan knew that was his opening. He proposed. She said yes. He slept well that night. She could barely sleep. A crazy and amazing story to start off this exciting new chapter.