Caitlyn and Christian both attended Michigan State University where Caitlyn was a member of Kappa Delta Sorority and Christian was a member of Lambda Chi Alpha Fraternity. It was one fateful Wine Wednesday when Caitlyn made her way to a party hosted by Lambda Chi. Caitlyn and Christian struck up a conversation over a game of cards, something that remains a staple in their relationship now. Christian couldn't take his eyes off of Caitlyn at the table. He asked for her number before she left, and luckily, she obliged. Little did they know that their lives were changed forever.

On a chilly winter day in New York, Christian convinced Caitlyn that he wanted to do some holiday activities in the city. She would later say that he was acting strange the whole time and wasn't as sneaky as he had initially thought. They went into Central Park to walk around, and when they reached the end of the Mall, Christian suggested they take a picture. Caitlyn said a selfie would do, but Christian said he would much rather ask someone else to take it. After finding a group of people to help, Christian and Caitlyn stood next to each other... Christian turned to Caitlyn... Christian got down on one knee... Caitlyn said YES! After a few more photos and phone calls to family, they went to Bemelmans Bar to celebrate, then enjoyed the Christmas Tree at Rockefeller Center and dinner at Le Coucou. It was the perfect day.