Kenny and Katie met through mutual friends in August 2019. Katie had recently moved to Annapolis with her sister and sister's now fiancé , John. Kenny was still living in Southern Maryland, but spent many weekends in Annapolis hanging out with his friends Sam & Allie. Sam knew Katie through his younger sister Molly and suggested setting Kenny and Katie up, but Molly told him Katie wasn't interested in dating. Then a few weeks later, Molly invited Katie to join Allie's bachelorette party celebrations in Annapolis. Katie thought it would be weird as she didn't know Allie, but Molly convinced her it would be fun and she would meet new people in the Annapolis area. So Katie went with Molly, met Allie and celebrated her upcoming marriage to Sam. Sam and his friends joined the group later in the day and Sam decided to take matters into his own hands. Sam FaceTimed Kenny and tried to introduce him to Katie, but instead Sam bumped into Katie's table, knocked it over, and covered her in drinks. Instead of the normal reaction to having drinks spilled on you, Katie started laughing, not knowing Kenny had seen the whole debacle. Even though she was still a stranger, Kenny realized in that moment Katie was different and he had to get to know her. The two finally connected later in the night, and the next day Kenny asked Katie out to dinner. Kenny & Katie went on their first date a week later at Tsunami in Annapolis. They instantly hit it off and talked for hours while walking around downtown. Kenny kept asking Katie to go on dates and before they knew it, they were spending every weekend together. Kenny ended up moving to Annapolis and they continued spending more and more time together falling in love. They spent weekends enjoying the Annapolis food scene, being on the water, hiking with Tucker, fishing (obviously), visiting family and friends, and taking trips to new places. In July 2021, they moved in together with Mr. T (Tucker). Over the last four years, Kenny and Katie have navigated the highs and lows of life as a team. They support each other and truly bring out the best in each other. On October 29th, 2022, Kenny asked Katie to spend her life with him and she said yes!