Jess and Glenn met through mutual friends at Boot Night in June 2022. Close to the end of the night, Jess asked for Glenn's number. At first, they decided to be friends, but 3 long months later, Glenn started falling for Jess and asked her to be his girlfriend August 31, 2022. They celebrated their one year anniversary with a trip to Denmark. Once Jess was a registered nurse in 2024, they took the next step and began living together. You know, to make sure the two Type A people could function together. Glenn became a registered nurse in the beginning of 2025 and began planning the proposal. Glenn proposed on June 19, 2025 by recreating the first official date by going to Leo's, a rooftop bar, proposing on top of a parking structure, and then finishing the night with an engagement celebration at Jess's parents house.