Clare and Jayson met in college at Northwest Missouri State during Clare's freshman year and Jayson's sophomore year. Clare and a friend went out to celebrate St. Patrick's Day weekend and found themselves at a large house party near campus. While sitting inside, Jayson approached Clare asking what her and her friend were discussing, which Clare told him it's none of his business. Clare soon found out that this was Jayson's birthday party so proceeded to be nice to him to get some cake.

Jayson remained persistent in getting Clare to talk to him, so they exchanged information and went their separate ways. A few months later, Jayson sent Clare a message in which he didn't expect a response. When she did respond, they spent most of the summer texting until the next fall semester.

At the start of the fall semester, Clare was sitting in her literature class when Jayson walked in, somehow he was also enrolled in the same class. Clare ignored Jayson throughout the entire class hoping he wouldn't recognize her. At the end of the class, Jayson sent Clare a text that said, "are you just going to ignore me?"

Jayson proposed to Clare on their trip to Scotland. The bus taking them from Glasgow to Glencoe stopped along a mountain range called The Three Sisters for a photo opportunity. Clare went out to walk around and see the mountains while Jayson stayed behind to "grab some Advil". Once they met up to take a picture, he popped the question!