Jackson and Maggie met in high school in 2016 when they both participated in their school's theatre production of The Crucible. At this time, they were barely even acquaintances; just two people who happened to be in the same theatre spaces at the same time for the next couple of years. Fast forward to fall 2018: Maggie was a senior in high school and Jackson a junior. They both had roles in The Laramie Project and shared a free-study period in the school's band room. When walking out of our rehearsal with a few friends, Jackson noticed Maggie's unique car: a yellow PT Cruiser. He complimented her on the car and, since that day, would walk her to her car everyday after school. They talked and hung out more and more each day during their study period and during rehearsal. One day, Jackson challenged Maggie to a Mario Kart tournament in school. In a nerdy (but cute) fashion, he said the loser has to tell the other one a secret. Maggie, in fact, lost; but Jackson was so eager to tell her his "secret" (Maggie felt it was adorably obvious that he had a crush on her) that he felt the need to tell her his confession anyway. He told her that he had feelings for her and she said that her "secret" (Maggie wasn't too subtle with her crush either) was the same. On October 18th, 2018, the two began dating after they exchanged a kiss after Jackson walked her to her car, just like any other day.

On December 23rd, 2023, Jackson proposed to Maggie after spending their day going on a holiday stroll at The Tuscan Village. After sipping on some overpriced boozy hot chocolate, the two drove back home. In the driveway, he hugged Maggie and asked if she was having a good day, to which she replied "yes, I'm having a great day!" Jackson replied comedically, "want me to make it better?" and he proposed. Elated, Maggie accepted his ring and showed the one that she got for him as well. By the time they get married, they will have been together for almost 7 years!