Kate and Jonathan met on Tinder in Indianapolis in the summer of 2017. Kate had just moved to Indy to work on Joe Donnelly's Senate campaign. Jonathan was one year out of the Navy and enrolled in college. Their first date was 90's Night at the Vogue Theater in Indianapolis -- they danced the night away and made each other laugh a lot. Kate and Jonathan saw each other the rest of that summer and started seriously dating in September 2017.

In December 2020, Jonathan and Kate and Kate's parents, Maureen and Dennis, stayed in Breckenridge on Peak 8. It felt magical being there just before Christmas––snow, lights, Christmas music, and, of course, tacky Christmas necklaces and headbands. The second night they were in Breck, December 13, Jonathan and Dennis tried to find a nice restaurant for dinner, but indoor dining was very limited due to the pandemic. So, instead, they decided to make dinner in the condo. Before dinner, Kate noticed that a gift bag she had brought with her was sitting under a tree outside the room where she and Jonathan were staying. She walked into the living room to ask what was going on, and her parents directed her outside to "take family photos." Kate brushed her hair and threw on a beanie, and made everyone put on the cheesy Christmas necklaces and headbands she brought with her. Jonathan was waiting by the tree outside their room and told Kate to grab the gift bag. Kate opened the bag, saw the ring box, and nervously handed it to Jonathan. It was snowing as he got down on one knee and asked Kate to marry him with their dog Griffin and Kate's parents there. The ring is a family heirloom from Kate's great grandmother Catherine Corrigan Oehl. It was a pretty perfect proposal!