Brittany and Stephen first met in passing during their freshman year at Illinois State University, but it wasn’t until their sophomore year when they became neighbors that they started getting closer. Their relationship began to blossom when they would walk to an accounting class they shared, with Stephen often letting Brittany copy his homework.

Spring break that year took them both to South Padre Island with their friends. The first time Stephen thought "I could picture myself marrying this girl" was on a night boat cruise in South Padre, where they spent the entire night talking and became inseparable. This newfound connection continued when they returned to ISU, and they made their relationship official shortly after.

They continued to date throughout college and into their new adult lives, both working and living in the city. In May 2023, they moved in together and Stephen realized that making Brittany wait eight years was long enough. He finally popped the question in Chicago in May 2024.