It all started with a horse. Cassidy and Tyler first met at Gulfstream Park on May 19, 2017. Tyler piloted e Five Racing's Mizz Money to victory that day. Then, in August, the pair met again when Tyler won aboard Cassidy's namesake, Cassidy's Reward. However, it wasn't until after the Breeders' Cup later that year that Cassidy and Tyler took their relationship to the next level. After their first date, the pair were inseparable. A few months later, the couple moved in together. Over the years, Cassidy and Tyler have made many memories together: traveling, celebrating tremendous career wins for Tyler, adult milestones, learning the ropes, and adding multiple four-legged members to their family. In 2020, the couple purchased their first home in Louisville, KY. Fast forward to July of 2021. Tyler surprised Cassidy with a vacation to the Florida Keys. The couple took a boat over to Little Palm Island and spent some quality time together. That night, the pair went to dinner, following a path of roses to their oceanside table. Cassidy was completely unaware of Tyler's big plans. On July 7, 2021, Tyler asked Cassidy to marry him. And with that, a new chapter begins! 🤍