In the fall of 2021, Jessie needed a date to her Tri Delta formal. As she did many times throughout her time at Butler, she decided to ask her trusty big Vicki for help. After asking Vicki if she knew of anyone willing to go to formal, Vicki sent her an instagram account of a guy named Spenser. Jessie's big and Spenser's big coordinated, and soon after Jessie was given Spenser's phone number and was told to text him to confirm he wanted to go to this formal. Since then, the two have never stopped texting.

On June 19th, 2025, Jessie and Spenser were driving up to Pentwater, Michigan for their third trip to Spenser's family's lake house. This was the same night as Game 6 of the NBA finals, so their plan was to drop off their things at the house and head into town to grab dinner and cheer on the Pacers. Once they reached the house, Spenser asked Jessie if she wanted to make a quick stop to the beach. The two of them walked down to the beach, with nobody else in sight, and enjoyed the view for a minute. As they were about to take a walk through the beach, Spenser turned Jessie around to face him. As Jessie turned, she found Spenser on one knee, asking her to be his wife. After a speechless 20 seconds, Jessie finally said yes, and the rest is history!