Jackson and Meghan met when they were both in school at the University of Louisville. They were both on the competitive cyber defense team (nerds) and were working on completing the same degree. Meghan spent a couple months trying to get his attention by asking him school and tech related questions and with help on building a Discord bot (nerds again). Finally, Jackson began to talk to her about other topics beyond school and the rest is history.

Jackson leading up to the proposal had a few items to check off. Jackson had initially planned this trip as a vacation, since the flights were cheap. However, seeing his opportunity he put his plan into action. Jackson talked with his parents and siblings first to make sure his mind was in the right place. Then came the talk with Meghan's parents. Stressful but they approved too. Finally came the talk with his grandma. The ring had to be his grandma's engagement ring, with the diamond being Jackson's great-great-grandpa's. Making it down to St Pete Beach, they enjoyed their time until Sunday, July 23rd. That night he had planned a visit to 1200 Chop House and walk back on the beach since the sun would be setting soon. During the meal though, Meghan had noticed her friend Isabella was nearby. Jackson tried to downplay this, but the secret had potentially been leaked. On the walk back on the beach, Jackson spotted Isabella. Once in the right spot for photos, he bent down on one knee and asked the question.