Dawson and Anna were neighbors for 13 years, but did not meet until June 2015 after Dawson invited Anna over for a game of basketball. After this encounter Dawson and Anna started hanging out more frequently once they started attending Nedrose High School that fall. After 6 persistent months Anna agreed to go on a date with Dawson. They've now been dating 5 years and have been enjoying their time together doing many activities such as golfing, skiing, traveling, and much more.

Dawson, Anna, and her family headed to Elgin, ND for the weekend to visit the Schatz grandparents. Everyone was gathered in the living room when Dawson surprisingly got down on one knee and asked Anna to marry him. She excitedly said YES! Later that day Dawson and Anna went for a drive out to Medicine Rock just south of Elgin to explore. There Dawson stated that this was the kind of place he had imagined proposing to Anna but wanted her family to be there. After that he got down on one knee again, and proposed more intimately just him and her on top of that hill. It was a day filled with love and excitement.