Kirk was hired at Matrix Brokerage in September 2019, and Madison was hired in March of 2020. Thanks to COVID, they never met until Spring of 2021 at a trade show. They spent hours talking one night and Madison invited Kirk to dinner (yes, she made the first move!) and asked Kirk how he felt about her. At first, he was nervous about pursuing Madison, but eventually asked her on a date to a hibachi restaurant, and the rest is history!

Kirk had the ring for weeks after asking Madison's dad, Bennett, for her hand in marriage. He passed away in November 2021 from pancreatic cancer, and her mom, Angie, had invited all of the family down to Edenton to spread his ashes. Family was the most important thing in the world to Bennett, and Kirk saw the opportunity to ask Madison to be his wife in front of the people who meant the most to her. He asked Angie if he could propose that weekend, and she of course said yes. Angie planned a "family photoshoot" on the dock at sunset. Madison's sister, Liz, told Madison to turn around and look at the water, recreating an old childhood photo. When Madison turned around, Kirk was down on one knee asking her to marry him.