Ally and Jonah met after a Women's Chorus performance, where a mutual friend introduced them. Later that night, they met once again at Hurricane Harry's, a former dance hall in College Station where they two-stepped together. About 6 months later, Jonah asked Ally to be his date to the Air & Space Force Ball after an Open Rehearsal. With the support of his buddies, Jonah started to pursue Ally more seriously, studying with her, taking her out for dinner at Piada, and then finally taking her on the field for a Midnight Yell Practice where they had their first kiss. They started dating officially the night before the Air Force Ball.

The proposal was a well-kept secret, with almost each one of Ally and Jonah's friends knowing about it except for Ally. Jonah wrote an 8-page document (OPORD) detailing every step of the proposal, which included sending his iPad with his location to Houston to convince Ally that he was out of town at a Singing Cadets Concert. Ally was told to dress up for what she believed was a friend’s graduation pictures, and an entire photo shoot was staged to throw her off from the actual event. When heading to dinner after the pictures, Ally's friends instead drove her to Albritton Clocktower, where Jonah was waiting to propose. The proposal ended with a saber arch and a surprise engagement party at Ally's house.