Alison and Jack met at their H-E-B internship the summer after their sophomore year of college. First, a friendship blossomed, and by the end of the summer, they did not want to say goodbye. Jack went back to College Station, and Alison headed up to Austin for the fall semester. However, Jack came up with multiple excuses to "casually" be in Austin the first few weekends of the school year, and these dates budded into a relationship shortly after.

Alison and Jack took a whirlwind visit to Jackson Hole, Wyoming in October. Lauren, Rachel, and Kara tagged along on an alleged "nature drive" through Grand Teton National Park where Jack stopped at a picturesque spot overlooking the Teton mountains and asked Alison to marry him.