Lily and Jack first became friends Fall of 2017 where they sat next to each other in high school band. After they became friends, they would constantly tease and banter with each other. They were competitive on who got the solos for concerts and would bicker on who was the best euphonium player. Outside of band, they connected at mutual friends' houses and went put-putting together that next Summer. Lily confessed that she had a crush on Jack during that time and Jack admitted that he had a crush on her too, but was more focused on heading to his freshman year at Western Michigan University. Jack and Lily would also play iMessage games with each other outside of school, where their teasing and flirting continued.

Lily and Jack reconnected near Christmas of 2019 by playing iMessage games. After Lily had beat Jack in a game of 8-ball pool in one turn, Jack had told her, "that was impressive, if you can do that again, I'll take you to get coffee sometime." Lily quickly beat Jack in 8-ball yet again. They had their first date at Jackson Coffee Company where they played cards and talked.

Lily and Jack had just gotten back from a weekend in Kalamazoo, where they watched a Hockey game with Darryck and Lillian Walker. It was a sunny December day and they were planning on going on a walk, which is a common activity that they do. They decided on the Dahlem Center conservatory, where they walked for about a mile, around the big meadow, when Jack told Lily that he wanted to go near the big trees on the edge of the field. He then jokingly said, "relax, I just want to take some pictures." Lily did not expect anything until they were going up the path to where the trees were, where she noticed that her heart was pounding in her chest and Jack was avoiding eye contact. During that time he was really concerned on how he was going to get the ring out of his coat pocket. They reached the trees where Lily turned around to look at a dead little pine tree and joked, "look, this can be our Christmas tree this year." When Lily turned back around, she saw Jack on one knee holding the most gorgeous ring she'd ever seen. Lily's first thought was, "holy shit," but tried extremely hard to keep the moment romantic and only said it out loud after she had said "yes."