Ashley and Jordan both attended and graduated from Boone County High School in 2015. Jordan knew Ashley, but Ashley did not know Jordan. According to Jordan, there was a day that he saw Ashley walking in the hallway at school and from that moment he knew he wanted to meet her. While that did not happen in high school, he did find an opportunity near the end of 2019. Ashley looked at Jordan as an amazing friend until 2021 when things started to change for the better. This great friendship turned into a relationship on April 12, 2021.

Ashley had always dreamed of taking a cruise to Bermuda. Near the beginning of 2022, the couple decided they were going to book the trip, and this is when Jordan started planning for bigger things. After over a year of waiting, Ashley and Jordan jumped on the MSC Meraviglia and started their journey to Bermuda on September 18, 2023. While on a bus tour on September 21, 2023, Jordan was searching for the perfect beach to propose on. After visiting a quiet beach with gorgeous pink sand, Jordan felt like that would be the perfect place to return to that evening. Little to his surprise, Ashley had enough of the sun and wasn't sold on returning to the beach that evening. The next stop on the tour was Gibb's Hill Lighthouse. Somewhere between the bus ride and the proposal, Jordan slipped the ring in his pocket just in case the lighthouse showed as a promising site. While up there, Ashley was amazed by the view and this is when Jordan found a person to take a video, or what Ashley thought was a picture. While smiling for said picture, Jordan got down on one knee and proposed.