Prior to Covid, Oliver was living in Tampa working at a hotel & Kylie was hardly in Orlando with the constant work travel. Being both in the hospitality industry, they came to a harsh reality once Covid started and their individual lives were disrupted. Oliver was forced to moved back to Orlando and Kylie was grounded in Orlando both unsure if their industries would recover. With all of the hardship during that unprecedented time in life, they found the silver lining remembering without Covid Oliver & Kylie may have never met. Oliver & Kylie were both active on a dating app called Hinge. Kylie vowed to never swipe right on an FSU alumni as it didn't fit her "lifestyle", but one day that all changed when she saw Oliver's profile. She noticed he was also in the hospitality industry and figured it would be refreshing to talk to someone who understood what she was going through with the Covid uncertainty. They decided to go to dinner at a Mexican restaurant in Baldwin Park. They ordered margaritas & queso and talked non stop, ending up missing out on ordering dinner because the kitchen closed. In Covid fashion, they took to-go margaritas to continue their conversation down by Lake Baldwin. With Tucker's approval, Oliver & Kylie have been inseparable ever since and still never run out of things to talk about. Over the past three and a half years, they have supported each other through a long-distance relationship for a year, have travelled to over 20 cities around the US together, and have successfully survived three football seasons as "rivals".

After Oliver received permission from Kylie's father, he would think long and hard about how to make the proposal as special as possible, but there were several things that had to happen before he could pop the question. Once the ring was decided, an idea was born. An idea of trying to bring our families together to celebrate this great occasion. The idea of a New Smyrna Beach proposal was becoming more and more popular as this was a place that both Kylie and Oliver love, and somewhere they spent one of their first dates. But how to pull this off? With some amazing detective work by both moms a plan was developed. The plan: Oliver's parents rented a condo in NSB for the weekend, Oliver told Kylie that his parents wanted all of his brothers and their significant others to come so they could take a special photo for his parent's anniversary, Kylie's parents would secretly also be in NSB, and we would all celebrate after. The execution: Oliver went to NSB a day early to get the nerves out and find a spot. After a spot was decided and a photographer was chosen, he was ready. Kylie drove down the next day expecting to meet up with Oliver and take a photo. Once on the beach, Oliver told Kylie that his family was running late but he knew the spot they were to meet everyone. As they approached the spot, Oliver instantly forgot all the things he wanted to stay but was able to pop the question. Hidden in the bushes was Oliver's brother Ben to capture the moment. After celebrating with a few glasses of champagne, they were ready to head back to the condo to tell Oliver's parents, as Oliver told Kylie only Ben knew his plan. Kylie still had no idea that her parents were aware of this and upstairs waiting. This was the 2nd big surprise of the night. When they got back to the condo, her parents surprised her and both families celebrated with great food, drinks, laughs, and plenty of photos.