Jeffrey and Cassie were high school sweethearts, and first met in their ninth grade health class. Cassie and Jeffrey didn't get along at first, but soon they became friends. Later on, during October of sophomore year, Jeffrey randomly decided to text Cassie. Two weeks later, Jeffrey and Cassie began dating. They went to junior and senior prom together. After graduating high school, they attended Georgia Southern University together.

After a short five years (or an eternity, depending on who you ask), Jeffrey finally mustered up the courage and money to buy a ring. Then, using his 21st birthday as a cover, had family and friends gather in Cassie's duplex apartment in Statesboro for the proposal. After opening a few birthday gifts, Jeffrey excused himself to the other room to retrieve the ring. As he walked back into the living room, his friend started What A Man Gotta Do by The Jonas Brothers, and it was on. He asked her to stand up, nodding to her as she asked 87 times "is this for real". After trying to decide which leg to get down on, he revealed the ring to her. And, in his words, because he was so taken back by the twinkle in her eye, Jeffrey never actually asked the question, but Cassie accepted the ring anyways.