Although they went to the same high school, Jasmine (a band nerd) had no idea who the older football player was. It wasn't until the summer after she graduated in 2017 that they met through a mutual friend. Jasmine and her friend had an extra ticket to a Chicago Cubs game and looked everywhere to get someone to take it. When her friend suggested they invite someone named Kyle Gunderson, Jasmine thought nothing of it. As soon as they met, though, Jasmine immediately knew that he was going to be her next boyfriend. After the Cubs game, they exchanged phone numbers and have been inseparable since.

Jasmine and Kyle had been doing a date night every month and took turns planning them. One month, Jasmine would plan something that Kyle knew nothing about, and the next month, Kyle would plan a date night that Jasmine knew nothing about. For their date in June 2024, Kyle had planned a hike at Waterfall Glen, which also happens to be their first date spot. It was a miserable day: 95°, extremely humid, and sunny. Partway into the hike, Jasmine told Kyle, "Let's just go home", but Kyle was determined to get to the overlook spot at the top of the hill. With a bag of dog waste in hand, they finally reached the top where there were rose petals and a floral arch with the words "Will you marry me?" on a neon sign. At first, Jasmine thought the proposal was for someone else, so she tried to pull Kyle away so as not to ruin someone else's special moment. It wasn't until Kyle said her name multiple times that she noticed all the framed pictures of them lining the walkway and Kyle getting down on one knee. Obviously, she said yes (but not before bursting out into tears and asking if they had to finish their hike).