Kyle and Caitlin met through mutual friends during their high school years. They had been apart of the same friend group for many years, until October 2020 when Kyle asked Caitlin on their first date. On October 2, 2020 Kyle and Caitlin met at Top Golf for dinner and a round of golf. Even though they were both nervous, and Kyle spilled his drink all over their dinner, they had an amazing time and followed up with a second date the next weekend. They have been inseparable since. So inseparable that the longest amount of time they spent away from each other was the 5 days in 2023 that Caitlin was in Destin, Florida before Kyle flew down to meet her and propose.