Dylan proposed almost one year after they started dating. To Olivia, it was just another beautiful Saturday but little did she know Dylan had been planing for weeks. On Saturday, May 20, 2023 on a private catamaran on the Amelia River in front of Olivia's grandmother's house, Dylan pulled off the biggest surprise of Olivia's life.

Dylan had recruited the help of Olivia's cousin Kayla and her boyfriend Brent. They asked them to join them on a boat cruise Kayla had won at work. Olivia, of course, didn't think much of it and asked if Dylan was available on Saturday to go up to Amelia and spend the day with Kayla and Brent. The boat sailed down the Amelia River unknowingly they were going to sail right past Olivia's grandmother's house. As Olivia pointed out all the landmarks, they started to pass by her grandmother's house and that is when Dylan turned to Olivia and got down on one knee. At this point everything was a blur as Olivia was overcome with emotions. To make it even more special both of their families were at the end of her Aunt's dock just a few houses down waiting for them. They had seen the whole thing happen. Even Olivia's Gran was wheeled down the dock, oxygen tank in tow. And Olivia's Uncle shot off fireworks even though it was in the middle of the day. They popped champagne and celebrated at dinner at Brett's Waterway cafe, a family favorite. The day could not have been more perfect.

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