Austin and Bailey met at their New Titan Day at Westminster College. Bailey's mom, Karen started referring to Austin as "Jeep Boy" because of his Facebook profile picture. Once the semester started, Bailey and Austin began talking, and had an immediate connection. They started dating on October 12th, 2016.

In August of 2017, Austin and Bailey decided to go on their first vacation together in Erie, Pennsylvania where they went camping on the beach. They had set up their tent, and went to grab dinner and go to an arcade… When they came back, the waves were so high they ate up most of the beach. The water began entering their tent with all their stuff... and Bailey's promise ring unbeknownst to her. Austin would give Bailey her promise ring at the Cheddar's in Erie, promising to replace it someday with an engagement ring.

On June 11, 2019, Austin and Bailey took a hike up to the highest peak in the Smokey Mountains on their vacation to Tennessee. After nearly dying on the trek up the mountain, they finally reached the peak, Clingman's Dome. Austin asked a nearby sightseer to take their photo and whispered that he was going to propose to her! As they were taking pictures, Austin got down on one knee and proposed! All Bailey could keep saying was "Yes!"